- Nucleophilic addition to 3-methyl-1-(4-nitrophenyl)-2-phenyl-4,5-dihydroimidazolium iodide
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Reactions of the 1,2-diaryl 4,5-dihydroimidazolium, represented by 3-methyl-1-(4-nitrophenyl)-2-phenyl-4,5-dihydroimidazolium iodide 1, with ethylenediamine afforded a benzylidyne unit transferred product, 2-phenyl-2-imidazoline 2; a ring-opened adduct 4 was produced when excess ethylenediamine was used. Reactions of 1 with hydroxylamine, malononitrile, and nitromethane anions produced ring-opened products, 5, 7, and 8 respectively.
- Xia,Tang,Zhou
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- A cobalt coordination polymer from bulk to nanoscale crystals as heterogeneous catalysts for tandem reactions
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Constructing nanoscale coordination polymers (CPs) with different micro- or nanoscale morphologies and sizes is crucial for the functionalization of CPs-based heterogeneous catalysts. Herein, surfactant polyvinylpyrrolidone (PVP), surface-supported frameworks (filter paper or Ni foam), and Co-based CPs (1), [Co2(pdpa)(py)4(H2O)]n (H4pdpa ?= ?5,5’-(pentane-1,2-diyl)-bis(oxy)diisophthalic; py ?= ?pyridine)) were employed to develop highly ordered micro- or nanoscale CPs, achieving microscale 1a (without surface-supported framework) and nanoscale 1b-c (filter paper and Ni foam as surface-supported frameworks for 1b and 1c, respectively). Furthermore, the catalytic performance of nanoscale 1c with spheric particles for the tandem conversion reactions of aromatic nitriles and diamines into imidazoline or tetrahydropyrimidine frameworks was much more prominent than that of large scale 1, microscale 1a, and nanoscale 1b because of the easily accessible catalytic active sites in the nanoscale spheric particles, which offered a functionalizable platform for the tandem reactions by minimizing the diffusion distance but did little for their activity.
- Han, Suzhen,Wang, Wenjie,Lu, Guizhen,Wang, Di,Zhang, Ying-Ying,Shao, Zhichao,Huang, Chao
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- Visible Light-Promoted Aryl Azoline Formation over Mesoporous Organosilica as Heterogeneous Photocatalyst
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N-heterocyclic compounds demonstrate wide applications ranging from natural compound production to coordination chemistry. Usually, the synthesis of N-heterocyclic compounds is conducted under thermal conditions, mostly by Lewis acids or metal-containing compounds as molecular catalysts. Here, we report a photocatalytic route for aryl azoline formation by mesoporous organosilica as visible light-active and heterogeneous photocatalyst. Via formation of aromatic aldehydes with various amines, 2-phenyl-2-imidazoline, 2-phenyl-2-oxazoline, 2-phenyl-2-thiazoline and their derivatives could be formed with high conversion and selectivity. Additionally, the organosilica photocatalyst showed high stability and reusability.
- Wei, Wenxin,Li, Run,Huber, Niklas,Kizilsavas, G?nül,Ferguson, Calum T. J.,Landfester, Katharina,Zhang, Kai A. I.
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p. 3410 - 3413
(2021/05/29)
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- A 2 - phenyl imidazoline and pyromellitic anhydride adduct preparation method and application of (by machine translation)
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The invention relates to a 2 - phenyl imidazoline and pyromellitic anhydride adduct of preparation method, steps are as follows: (1) synthesis of 2 - phenyl imidazoline; (2) the step (1) synthesis of 2 - phenyl imidazoline equimolar proportion of pyromellitic anhydride is added drop solution or suspended in the emulsion, to carry on the reaction to produce salt adduct, then through the centrifuge, cyclone drying, trap collection, to obtain 2 - phenyl imidazoline and pyromellitic anhydride adduct. This method not only in the final product containing organic amine functional groups, and also containing carboxylic acid functional group, the compound has imidazole catalytic curing function and the reaction of the carboxylic acid function, is mainly applied to the lusterless powder coating field, mainly plays the role of the elimination of gloss, can make the coating achieves a low gloss, or even completely matt artistic effect, and other general material it is difficult to meet such a requirement, it can be used as the epoxy resin curing agent, can also be used for other fields of the epoxy curing agent or catalyst. (by machine translation)
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Paragraph 0039-0045
(2019/06/30)
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- Green Synthesis of 2-Substituted Imidazolines using Hydrogen Peroxide Catalyzed by Tungstophosphoric Acid and Tetrabutylammonium Bromide in Water
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Various 2-substituted imidazolines were constructed from aromatic aldehydes with ethylenediamine using hydrogen peroxide as an oxidant in water. Tungstophosphoric acid (HPW) was found to be active for this transformation due to its ubiquitous catalytic and oxidative nature, and further combination of tetrabutylammonium bromide (TBAB) made this transformation more efficient and attractive. It was found that the yields of the corresponding 2-substituted imidazolines were markedly influenced by the position and nature of the substituents on the phenyl ring. A plausible mechanism was also proposed to clarify this catalytic oxidative system.
- Liu, Shuai,Li, Wang,Pang, Yiying,Xiao, Hesheng,Zhou, Yi,Wang, Xiaoji
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p. 998 - 1002
(2019/02/05)
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- A novel ternary GO@SiO2-HPW nanocomposite as an efficient heterogeneous catalyst for the synthesis of benzazoles in aqueous media
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A new solid acid catalyst, consisting of 12-phosphotungstic heteropoly acid (HPW) supported on graphene oxide/silica nanocomposite (GO@SiO2), has been developed via immobilizing HPW onto an amine-functionalized GO/SiO2 surface through coordination interaction (GO@SiO2-HPW). The GO@SiO2-HPW nanocomposite was characterized by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and powder X-ray diffraction (XRD). The prepared nanocomposite could be dispersed homogeneously in water and further used as a heterogeneous, reusable, and efficient catalyst for the synthesis of benzimidazoles and benzothiazoles by the reaction of 1,2-phenelynediamine or 2-aminothiophenol with different aldehydes.
- Habibzadeh, Setareh,Firouzzadeh Pasha, Ghasem,Tajbakhsh, Mahmood,Amiri Andi, Nasim,Alaee, Ehsan
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p. 934 - 944
(2019/06/13)
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- Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines
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A novel synthetic methodology for the assembly of imidazolines via an unusual reaction between nitroalkanes and aliphatic 1,2-diamines in the presence of phosphorous acid is described. In contrast to the related highly efficient preparation of benzimidazoles from aromatic amines, this process represents a major synthetic challenge and for a long time was elusive. Analysis of the method limitations is provided.
- Aksenov, Alexander V.,Aksenov, Nicolai A.,Arutiunov, Nikolai A.,Malyuga, Vladimir V.,Ovcharov, Sergey N.,Rubin, Michael
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p. 39458 - 39465
(2019/12/14)
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- Cu(II) immobilized on Fe3O4@Agarose nanomagnetic catalyst functionalized with ethanolamine phosphate–salicylaldehyde schiff base: A magnetically reusable nanocatalyst for preparation of 2-substituted imidazolines, oxazolines, and thiazolines
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Herein we synthesized Cu(II) immobilized on Fe 3 O 4 @Agarose functionalized with ethanolamine phosphate–salicylaldehyde Schiff base (Fe 3 O 4 @Agarose/SAEPH 2 /Cu(II)) as a new and cost-effective nanomagnetic catalyst. The nanomagnetic catalyst was characterized by FT- IR, XRD, VSM, SEM- EDX, TEM, TGA, and ICP techniques and it was found that the particles were about 9–25 nm in size and spherical with entrapment of the Fe 3 O 4 particles in the hollow pore structure of the agarose. The prepared nanomagnetic catalyst showed excellent activity for preparation of 2-substituted imidazolines, oxazolines, and thiazolines. The catalyst is easy to prepare and exhibits higher catalytic activity than some commercially available copper sources. More importantly, this nanomagnetic catalyst can be easily recovered by using a permanent magnet and reused for at least seven cycles without significant deactivation.
- Zarei, Zeinab,Akhlaghinia, Batool
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p. 170 - 191
(2018/02/17)
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- Synthesis of tetrazoles, triazoles, and imidazolines catalyzed by magnetic silica spheres grafted acid
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The magnetically separable catalysts are used in the synthesis of N-containing heterocycles, including tetrazoles, triazoles, and imidazolines. The magnetic silica sphere grafted sulfonic acid (MSS-SO3H) is suitable for the synthesis of 1,2,3-triazole via the cycloaddition of nitroalkene with NaN3, whereas the zinc-modified silica sphere catalyst (MSS-SO3Zn) is more suitable for the synthesis of tetrazoles. The MSS-SO3Zn catalyst also works well for the synthesis of 2-substituted imidazoline via the condensation of nitriles with ethylenediamine. Both of the MSS-SO3H and MSS-SO3Zn catalysts can be recovered easily by a magnet, and they can be reused without further tedious activation.
- Jiang, Ruihang,Sun, Hong-Bin,Li, Shuang,Zhan, Kun,Zhou, Junjie,Liu, Lei,Zhang, Kai,Liang, Qionglin,Chen, Zhangpei
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supporting information
p. 2652 - 2662
(2018/11/26)
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- Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons
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Novel imidazoline derivatives were synthesized from the norbornene and dibenzobarrelene skeletons which were obtained by the Diels-Alder reactions of anthracene and cyclopentadiene with the different dienophiles, such as fumaronitrile and fumaric acid. Synthesis of the C-2 substituted imidazolines was performed with high yields from various dinitriles and diacyl dichlorides.
- ?apan, Irfan,Servi, Süleyman
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supporting information
p. 131 - 142
(2018/10/26)
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- Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine
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Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.
- Vasilevsky, Sergei F.,Davydova, Maria P.,Mamatyuk, Victor I.,Tsvetkov, Nikolay,Hughes, Audrey,Baranov, Denis S.,Alabugin, Igor V.
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p. 421 - 429
(2017/04/07)
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- Synthesis of benzimidazole and quinoxaline derivatives using reusable sulfonated rice husk ash (RHA-SO3H) as a green and efficient solid acid catalyst
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In this work, a simple, rapid and efficient method for the preparation of benzimidazoles and quinoxalines from the condensation of o-phenylene diamines with aldehydes and/or 1,2-dicarbonyl compounds in the presence of sulfonated rice husk ash (RHA-SO3H) as an efficient green catalyst is reported. RHA-SO3H can be easily prepared using a readily available organic compound by simple modification of rice husk ash. All reactions are performed under mild reaction conditions with high to excellent yields. The method is applicable to aromatic, unsaturated and hetero aromatic aldehydes. The advantages of this method are short reaction times, milder conditions, easy work-up, solvent-free conditions and catalyst reusability.
- Shamsi-Sani, Mahnaz,Shirini, Farhad,Abedini, Masoumeh,Seddighi, Mohadeseh
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p. 1091 - 1099
(2016/04/26)
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- Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetic nanoparticles: A novel catalyst for the synthesis of imidazole derivatives under solvent-free conditions
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New Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetite nanoparticles were prepared using a co-precipitation method and were used in the syntheses of imidazole derivatives under solvent-free conditions. The polyionene was easily prepared by reacting DABCO and 1,4-dibromo butane in DMF/methanol. It was then added to the previously formed layers and magnetic core-shell nanoparticles (P-MNPs) were functionalized. All the resultant nanoparticles were characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), infrared spectroscopy (FTIR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and vibrating sample magnetometry (VSM). The catalyst was readily recovered by simple magnetic decantation and can be recycled several times with no significant loss of catalytic activity.
- Dezfoolinezhad, Elham,Ghodrati, Keivan,Badri, Rashid
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p. 4575 - 4587
(2016/06/09)
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- Ruthenium(II) carbonyl complexes containing pyridoxal thiosemicarbazone and trans-bis(triphenylphosphine/arsine): Synthesis, structure and their recyclable catalysis of nitriles to amides and synthesis of imidazolines
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Pyridoxal N(4)-substituted thisemicarbazone hydrochloride ligands (L1-3) were synthesized and reacted with the ruthenium(II) starting complexes [RuHCl(CO)(EPh3)3] (EP or As). The resulting complexes [Ru(CO)(L1-3)(EPh3)2] (1-6) were characterized by elemental analyses and spectroscopic techniques. The molecular structure of complex 5 was identified by means of single crystal X-ray diffraction analysis. The catalytic activity of the new complexes was evaluated for the selective hydration of nitriles to primary amides and also the condensation of nitriles with ethylenediamine under solvent free conditions. The processes were operative with aromatic, heteroaromatic and aliphatic nitriles, and tolerated several substitutional groups. The studies on the effect of substitution over thiosemicarbazone, reaction time, temperature, solvent and catalyst loading were carried out in order to find the best catalyst in this series of complexes and favourable reaction conditions. A probable mechanism for both the catalytic reactions of nitrile has also been proposed. The catalyst was recovered and recycled in the hydration of nitriles for five times without any significant loss of its activity.
- Manikandan, Rajendran,Anitha, Panneerselvam,Prakash, Govindan,Vijayan, Paranthaman,Viswanathamurthi, Periasamy,Butcher, Ray Jay,Malecki, Jan Grzegorz
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p. 312 - 324
(2015/01/30)
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- Solvent templates induced porous metal-organic materials: Conformational isomerism and catalytic activity
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Solvent templates induced Co-based metal-organic materials; conformational isomers {[Co2(pdpa)(CH3CN)(H2O)3]·CH3OH·H2O}n (1) and {[Co2(pdpa)(CH3CN)(H2O)3]}n (2) and {[Co5(pdpa)2(μ3-OH)2(H2O)6]·2H2O}n (3) [H4pdpa = 5,5′-(pentane-1,2-diyl)-bis(oxy)diisophthalic acid] were synthesized under the same solvothermal conditions except with different concentrations of cyclic ethers (1,4-dioxane or tetrahydrofuran) as structure-directing agents. Structural transformations from a three-dimensional (3D) framework of 1 containing channels with dimensions of μ6 ? × 6 ? to a two-dimensional layer structure of 2 consisting of large open channels with a size of μ15 ? × 8 ? and then to a 3D nonporous framework of 3, resulting from the different concentrations of cyclic ethers, were observed. The anion-π interactions between electron-efficient oxygen atoms of cyclic ethers and electron-deficient dicarboxylic acid aromatic cores in H4pdpa imported into the synthetic process accounted for the conformational change of the ligand H4pdpa and the following structural variations. A systematic investigation was conducted to explore how different concentrations of structure-directing agents affected the frameworks of resultant metal-organic frameworks. Furthermore, 1-3 were shown to be available heterogeneous catalysts for the synthesis of 2-imidazoline and 1,4,5,6-tetrahydropyrimidine derivatives by the cascade cycloaddition reactions of aromatic nitriles with diamines. The results showed that the catalytic activity of 2 was much higher than that of 1 and 3, because of its unique structural features, including accessible catalytic sites and suitable channel size and shape. In addition, a plausible mechanism for these catalytic reactions was proposed, and the reactivity-structure relationship was further clarified.
- Ding, Ran,Huang, Chao,Lu, Jingjing,Wang, Junning,Song, Chuanjun,Wu, Jie,Hou, Hongwei,Fan, Yaoting
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p. 1405 - 1413
(2015/05/27)
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- Thermally triggered solid-state single-crystal-to-single-crystal structural transformation accompanies property changes
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The 1D complex [(CuL0.5H2O)·H2O]n (1) (H4 L = 2,2′-bipyridine-3,3′ ,6,6′-tetracarboxylic acid) undergoes an irreversible thermally triggered single-crystal-to-single-crystal (SCSC) transformation to produce the 3D anhydrous complex [CuL0.5]n (2). This SCSC structural transformation was confirmed by single-crystal X-ray diffraction analysis, thermogravimetric (TG) analysis, powder X-ray diffraction (PXRD) patterns, variable-temperature powder X-ray diffraction (VT-PXRD) patterns, and IR spectroscopy. Structural analyses reveal that in complex 2, though the initial 1D chain is still retained as in complex 1, accompanied with the Cu-bound H2O removed and new O(carboxyl)-Cu bond forming, the coordination geometries around the CuII ions vary from a distorted trigonal bipyramid to a distorted square pyramid. With the drastic structural transition, significant property changes are observed. Magnetic analyses show prominent changes from antiferromagnetism to weak ferromagnetism due to the new formed Cu1-O-C-O-Cu4 bridge. The catalytic results demonstrate that, even though both solid-state materials present high catalytic activity for the synthesis of 2-imidazolines derivatives and can be reused, the activation temperature of complex 1 is higher than that of complex 2. In addition, a possible pathway for the SCSC structural transformations is proposed.
- Li, Quan-Quan,Ren, Chun-Yan,Huang, Yang-Yang,Li, Jian-Li,Liu, Ping,Liu, Bin,Liu, Yang,Wang, Yao-Yu
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supporting information
p. 4703 - 4711
(2015/03/18)
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- Metal-free one-pot synthesis of 1,3-diazaheterocyclic compounds via I2-mediated oxidative C-N bond formation
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A one-pot I2-mediated annulation reaction of substrates containing diamino groups and aldehydes has been developed via oxidative C-N bond formation. This general and environmentally benign synthetic approach provides facile access to a variety of 1,3-diazaheterocyclic compounds, including quinazolinones, benzimidazoles, and cyclic amidines.
- Tian, Xianhai,Song, Lina,Li, Ertong,Wang, Qiang,Yu, Wenquan,Chang, Junbiao
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p. 62194 - 62201
(2015/08/03)
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- Efficient synthesis of 2-imidazolines in the presence of molecular iodine under ultrasound irradiation
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An efficient one-pot synthesis process for preparing 2-imidazolines from aldehydes and ethylenediamine using molecular iodine and potassium carbonate in absolute ethanol at 25-30°C under ultrasound irradiation is described. The synthetic strategy has the following advantages: mild conditions and low costs requirements, readily available catalyst, short reaction times, simplicity of operation, and good-to-excellent yields.
- Chen, Guo-Feng,Li, Hong-Yang,Xiao, Nan,Chen, Bao-Hua,Song, Ya-Li,Li, Ji-Tai,Li, Zhi-Wei
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p. 1516 - 1521
(2014/12/11)
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- Semi-empirical computation on mechanism of imidazolines and benzimidazoles synthesis and their QSAR studies
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A green, mild and anaerobic synthesis of imidazolines and benzimidazoles from aldehydes and diamines using I2/KI/K2CO3/H2O system has been investigated by semi-empirical methods. The observed efficient direction of the above synthesis has been modeled from a comparison of the energies of four possible transition states arising from mono and di additions of iodines in the configured molecules. In the reaction I1 B is the most favorable transition state [TS] which is shown to be 20 Kcal/mol by PM3 analyses. The resulting trends of relative transition states energies are in excellent agreement with the experimental observations. Also, the bond order, bond length, heat of formation is in good agreement to the formation of product B. In order to establish the suitable mechanism of the reaction a quantitative structure activity relationship analysis has been made using hydrophobicity as the molecular descriptor. In this analysis the values of refractivity, polarizability, hydration energy, electron affinity, ionization potential and dipole moment of the compounds have been correlated with their hydrophobicity which has been taken as the molecular property.
- Hazarika, Swapnali,Konwar, Dilip,Bora, Manas Jyoti
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p. 5073 - 5078
(2015/01/09)
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- Microwave-assisted cascade cycloaddition for C-N bond formation: An approach to the construction of 1,4,5,6-tetrahydropyrimidine and 2-imidazoline derivatives
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An efficient strategy for the synthesis of various 1,4,5,6- tetrahydropyrimidine and 2-imidazoline derivatives has been reported. The reactions proceeded from nitriles with ethylenediamine or 1,3-diaminopropane via cascade cycloaddition in the presence of CuL2 (L = 2-hydroxy-2-phenylacetate) to afford the corresponding 1,4,5,6- tetrahydropyrimidine or 2-imidazoline derivatives under reflux conditions or microwave irradiation in excellent yields.
- An, Shujuan,Yin, Bing,Liu, Ping,Li, Xiangnan,Li, Chen,Li, Jianli,Shi, Zhen
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p. 2525 - 2532
(2013/09/24)
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- Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis
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A mild, aerobic, catalytic process for obtaining nitriles directly from alcohols and aqueous ammonia is described. The reaction proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of O2. The substrate scope is broad including various functionalized aromatic and aliphatic alcohols. This protocol enabled the one-pot synthesis of various biaryl heterocycles directly from commercially available alcohols.
- Yin, Weiyu,Wang, Chengming,Huang, Yong
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supporting information
p. 1850 - 1853
(2013/06/04)
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- Cyclodehydration of N -(aminoalkyl)benzamides under mild conditions with a hendrickson reagent analogue
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Methods for the cyclodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducts.
- Loughlin, Wendy A.,Jenkins, Ian D.,Petersson, Maria J.
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p. 7356 - 7361
(2013/08/23)
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- Palladium-catalyzed multicomponent synthesis of 2-aryl-2-imidazolines from aryl halides and diamines
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An efficient palladium-catalyzed three-component reaction that combines aryl halides, isocyanides, and diamines provides access to 2-aryl-2-imidazolines in yields up to 96%. Through variation of the diamine component, the reaction can be extended to the s
- Geden, Joanna V.,Pancholi, Alpa K.,Shipman, Michael
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p. 4158 - 4164
(2013/05/22)
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- Trichloroisocyanuric acid as an efficient homogeneous catalyst for the chemoselective synthesis of 2-substituted oxazolines, imidazolines and thiazolines under solvent-free condition
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Trichloroisocyanuric acid, as a commercially available and inexpensive catalyst, was used in a new, facile and efficient procedure for the synthesis of 2-oxazolines, 2-imidazolines and 2-thiazolines through the reaction of nitriles with 2-aminoethanol, ethylenediamine or 2-aminoethanethiol under solvent-free conditions.
- Hojati, Seyedeh Fatemeh,Nezhadhoseiny, Seyede Atefe
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p. 1181 - 1189,9
(2020/09/14)
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- Microwave mediated solvent free synthesis of 2-arylimidazolines from aldehydes using a solid base catalyst
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2-Aryl imidazolines have been synthesized in solvent free condition using a catalytic amount of solid base (500mg) and by exposure to microwave. Ketones are not affected under these reaction conditions. Reaction time is short, clean products have been obtained and recovery is simple. The yields of the products are good.
- Das, Pranab J.,Baruah, Akashi
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experimental part
p. 752 - 755
(2012/06/30)
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- Efficient and one-pot catalytic synthesis of 2-imidazolines and bis-imidazolines with p-toluenesulfonic acid under solvent free conditions
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A practical, efficient, and inexpensive method for the synthesis of 2-imidazoline from the reaction of nitriles with ethylenediamine or 1,2-propanediamine using p-toluenesulfonic acid or pyridinium p-toluenesulfonate under reflux conditions is reported. This catalyst can be successfully applied for the chemoselective conversion of dicyanobenzenes to corresponding mono- and bis-imidazolines. The applications of these catalysts are feasible because of easy preparation, easy handling, stability, inexpensive, good activity, and eco-friendly.
- Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Mehrizi, Safie
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experimental part
p. 249 - 254
(2011/05/07)
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- Copper-catalyzed synthesis of 2-imidazolines and their N-hydroxyethyl derivatives under various conditions
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A rapid and efficient method for the synthesis of 2-imidazolines and their N-hydroxyethyl derivatives from the reaction of aromatic nitriles with ethylenediamine (EDA) or N-(2-aminoethyl)ethanolamine (AEEA) using cupric indole-3-acetate (Cu(II)-(IAA)2) as a reusable catalyst under reflux and microwave conditions is reported. And seven new N-hydroxyethyl-imidazolines were reported for the first time.
- Zhang, Jin,Wang, Xiao,Yang, Meipan,Wan, Kerou,Yin, Bing,Wang, Yunxia,Li, Jianli,Shi, Zhen
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experimental part
p. 1578 - 1582
(2011/04/26)
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- A facile and efficient synthesis of 2-imidazolines from aldehydes using hydrogen peroxide and substoichiometric sodium iodide
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The reaction of aldehydes with ethylenediamine for the preparation of 2-imidazolines has been studied using hydrogen peroxide as an oxidant in the presence of sodium iodide and anhydrous magnesium sulfate. A mild, green, and efficient method is established to carry out this reaction in high yield. Georg Thieme Verlag Stuttgart · New York.
- Bai, Guo-Yi,Xu, Kai,Chen, Guo-Feng,Yang, Yong-Hui,Li, Tian-Yu
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experimental part
p. 1599 - 1603
(2011/06/25)
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- An inorganic iodine-catalyzed oxidative system for the synthesis of benzimidazoles using hydrogen peroxide under ambient conditions
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A simple and efficient catalytic oxidative system for the synthesis of benzimidazole derivatives with H2O2 in the presence of catalytic amounts of Bu4NI is developed. The formation of highly reactive iodine (III) intermediate [Bu4N]+[IO 2]- is detected by ESI-MS for the first time, and a possible mechanism for the oxidation is proposed.
- Zhu, Chenjie,Wei, Yunyang
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experimental part
p. 1082 - 1086
(2012/04/17)
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- Dissecting alkynes: Full cleavage of polarized C≡C moiety via sequential bis-michael addition/retro-mannich cascade
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The reaction of diaryl ketoalkynes with 1,2-diamino ethane leads to the full scission of the triple bond with the formation of acetophenone and imidazoline fragments. In this transformation, one of the alkyne carbons undergoes formal reduction with the formation of three C-H bonds, whereas the other carbon undergoes formal oxidation via the formation of three C-N bonds (one π and two σ). Computational analysis confirmed that the key fragmentation step proceeds via a six-membered TS in a concerted manner. Both amines are involved in the fragmentation: the N-H moiety of one amine transfers a proton to the developing negative charge at the enolate oxygen, while the other amine provides direct stereoelectronic assistance to the C-C bond cleavage via a hyperconjugative nN → σ*C-C interaction.
- Roy, Saumya,Davydova, Maria P.,Pal, Runa,Gilmore, Kerry,Tolstikov, Genrikh A.,Vasilevsky, Sergei F.,Alabugin, Igor V.
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p. 7482 - 7490
(2011/11/30)
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- New transformation of α-acetylenic ketones under the action of 1,2-diaminoethane
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A reaction of 3-aryl-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ones with 1,2-diaminoethane in boiling dioxane leads to 2-aryl-4,5-dihydro-1H-imidazoles and 1-(3,4,5-trimethoxy-phenyl)ethanone.
- Davydova,Vasilevskii,Tolstikov
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experimental part
p. 188 - 190
(2011/08/21)
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- Efficient catalytic synthesis of 2-imidazolines and bis-imidazolines with silica supported tungstosilicic acid
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A rapid and efficient preparation of 2-imidazolines and bis-imidazolines by the reaction of ethylenediamine or 1,2-propanediamine with nitriles in the presence of catalytic amounts of tungstosilicic acid supported on SiO 2 under reflux condition, is reported. The advantages of this procedure are moderate reaction times, good to high yields and the ability to carry out the large scale reactions. ARKAT USA, Inc.
- Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Moghadam, Majid,Akhlaghia, Parisa
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experimental part
p. 97 - 109
(2010/08/04)
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- 1,3-Dibromo-5,5-dimethylhydantoin as an efficient homogeneous catalyst for the synthesis of 2-arylthiazolines and 2-arylimidazolines
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A simple, facile, and efficient procedure for the synthesis of 2-arylthizolines and 2-arylimidazolines has been developed by the simple condensation of nitriles with 2-aminoethanethiol or ethylenediamine catalyzed by 1,3-dibromo-5,5-dimethylhydantoin under solvent-free conditions. Selective preparation of bisthiozolines and monoimidazolines from dinitriles and also selective conversion of arylnitriles to their corresponding 2-arylthiazolines or imidazolines in the presence of alkylnitriles can be considered as considerable advantages of this method.
- Hojati, Seyedeh Fatemeh,Mohammadpoor-Baltork, Iraj,Maleki, Behrooz,Gholizadeh, Mostafa,Shafiezadeh, Fatemeh,Haghdoust, Mahnaz
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experimental part
p. 135 - 141
(2010/04/04)
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- Fragmentation of trifluoromethylated alkenes and acetylenes by N, N -binucleophiles. Synthesis of imidazolines or imidazolidines (Oxazolidines) controlled by substituent
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The reaction of β-halogeno-β-polyfluoromethylstyrenes with N,N- or N,O-binucleophiles leads to unexpected fragmentation products (imidazolines) or to heterocyclization giving CF3-substituted imidazolidines (N,N-) and oxazolidines (N,O-) depending on aryl substituent. The scope and the reaction mechanism are discussed.
- Nenajdenko, Valentine G.,Muzalevskiy, Vasiliy M.,Shastin, Aleksey V.,Balenkova, Elizabeth S.,Kondrashov, Evgeniy V.,Ushakov, Igor A.,Rulev, Alexander Yu.
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supporting information; scheme or table
p. 5679 - 5688
(2010/11/19)
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- Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors
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A series of sixteen 2-substituted-2-imidazolines (where the substituent R = Ph, Me-4-Ph; MeO-4-Ph; (MeO)2-3,4-Ph; (MeO)3-3,4,5-Ph; Ph-4-O-C(O)-Ph; Cl-4-Ph; Cl-2-Ph; Cl2-2,4-Ph; NO2-4-Ph; NO2-3-Ph; Naphth-2-yl; Fur-2-yl; Benzofur-2-yl; Pyridin-2-yl; Quinolin-2-yl) has been synthesized from the reaction of the substituted-aldehydes and ethylenediamine by ultrasound irradiation with NBS in an aqueous medium in high yields (80-99%). The 2-imidazoline ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated and some of them showed potent and selective MAO inhibitory activity especially for the MAO-B isoform and could become promising candidates for future development.
- Sant' Anna, Gabriela da S.,Machado, Pablo,Sauzem, Patricia D.,Rosa, Fernanda A.,Rubin, Maribel A.,Ferreira, Juliano,Bonacorso, Helio G.,Zanatta, Nilo,Martins, Marcos A.P.
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experimental part
p. 546 - 549
(2011/03/19)
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- Mild and efficient one-pot synthesis of 2-imidazolines from nitriles using sodium hydrosulfide as catalyst
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A simple and efficient method has been developed for the synthesis of 2-imidazolines through a one-pot reaction of various nitriles with ethylenediamine in the presence of sodium hydrosulfide as catalyst in high yield. Copyright Taylor & Francis Group, LLC.
- Sun, Min,Wei, Hong-Tao,Li, Dong,Zheng, You-Guang,Cai, Jin,Ji, Min
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p. 3151 - 3158
(2008/12/22)
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- Easy access to triazoles, triazolopyrimidines, benzimidazoles and imidazoles from imidates
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We have described a new and easy synthesis of triazoles, triazolopyrimidines, benzimidazoles and imidazoles variously substituted based on the reaction of imidates with diamine derivatives. The products were obtained in moderate to good yields. A general mechanism for the reactions is proposed.
- Zarguil,Boukhris,El Efrit,Souizi,Essassi
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body text
p. 5883 - 5886
(2009/04/05)
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- Rapid and efficient synthesis of imidazolines and bisimidazolines under microwave and ultrasonic irradiation
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Small assemblies of 2-imidazolines and bisimidazolines from appropriate nitriles and ethylenediamine with catalytic amounts of P2S 5 employing a microwave assisted protocol were prepared. Sonication of this system also led to successful synthesis of 2-imidazolines and bisimidazolines. Another advantage of these systems is the ability to carry out large scale reactions. Springer-Verlag 2007.
- Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Mirkhani, Valiollah,Tangestaninejad, Shahram,Abdollahi-Alibeik, Mohammad,Yousefi, Behrooz H.,Kargar, Hadi
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p. 579 - 583
(2008/02/03)
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- One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates
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Imidazolines were prepared in one-pot operation from aldehydes and diamines through oxidation of aminal intermediates by NBS. This method could be applied to various aromatic and aliphatic aldehydes and N-nonsubstituted and N-monosubstituted 1,2-diamines. Furthermore, it was found that CH2Cl2 could be altered to TBME, a more environmentally friendly solvent, in the reaction using N-nonsubstituted 1,2-diamines. The reaction conditions were very mild and chemoselective.
- Fujioka, Hiromichi,Murai, Kenichi,Kubo, Ozora,Ohba, Yusuke,Kita, Yasuyuki
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p. 638 - 643
(2007/10/03)
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- Facile preparation of 2-imidazolines from aldehydes with tert-butyl hypochlorite
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An efficient and high-yield preparation of 2-imidazolines was achieved from aldehydes and ethylenediamines in the presence of tert-butyl hypochlorite. By this method, 1,3-bis(imidazolin-2-yl)benzene and 2,6-bis(imidazolin-2-yl) pyridine, which act as chiral ligands, could be prepared directly from the corresponding dialdehydes in high yields. Georg Thieme Verlag Stuttgart.
- Ishihara, Midori,Togo, Hideo
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p. 1939 - 1942
(2008/02/10)
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- Palladium(0)-catalyzed, copper(I)-mediated coupling of boronic acids with cyclic thioamides. Selective carbon-carbon bond formation for the functionalization of heterocycles
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(Chemical Equation Presented) The palladium-catalyzed cross-coupling of cyclic thioamides with arylboronic acids in the presence of stoichiometric amounts of a copper(I) cofactor is described. The desulfitative carbon-carbon cross-coupling protocol is performed under neutral conditions and can be applied to a range of heterocyclic structures with embedded thioamide fragments. Successful carbon-carbon cross-coupling is independent of the ring size, aromaticity/nonaromaticity, the presence of additional heteroatoms, or other functional groups in the starting thioamide structure. Employing controlled microwave irradiation at 100°C, most cross-couplings can be completed within 2 h and proceed in high yields. An advantage of using thioamides as starting materials is die fact that the system can be tuned to an alternative carbon-sulfur cross-coupling pathway by changing to stoichiometric copper(II) under oxidative conditions. Both types of thioamide cross-couplings are orthogonal to the traditional base-catalyzed Suzuki-Miyaura cross-coupling of aryl halides with boronic acids.
- Prokopcova, Hana,Kappe, C. Oliver
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p. 4440 - 4448
(2008/02/05)
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- Desulfitative carbon-carbon cross-coupling of thioamide fragments with boronic acids
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A novel and general carbon-carbon cross-coupling reaction between cyclic thioamides and boronic acids is described. The reaction is catalytic in palladium(O) and requires stoichiometric amounts of a copper(I) carboxylate as metal cofactor. The mode of cross-coupling in the reaction of cyclic thioamides with boronic acids is easily tunable between carbon-carbon and carbon-sulfur cross-coupling. While the catalytic palladium(O)/ copper(I) system provides carbon-carbon bond formation with extrusion of sulfur, stoichiometric quantities of copper(II) under air mediate carbon-sulfur bond formation.
- Prokopcova, Hana,Kappe, C. Oliver
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p. 448 - 452
(2008/02/08)
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- Direct oxidative conversion of aldehydes and alcohols to 2-imidazolines and 2-oxazolines using molecular iodine
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Aldehydes were converted to the corresponding 2-imidazolines and 2-oxazolines in good yields by the reaction with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate. Moreover, primary alcohols were directly converted to the corresponding 2-imidazolines and 2-oxazolines via aldehydes in one-pot manner with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate.
- Ishihara, Midori,Togo, Hideo
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p. 1474 - 1480
(2007/10/03)
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- Rapid and efficient synthesis of 2-imidazolines and bis-imidazolines under ultrasonic irradiation
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Rapid and efficient preparation of 2-imidazolines and bis-imidazolines by reaction of ethylenediamine with nitriles in the presence of catalytic amounts of sulfur under ultrasonic irradiation is reported. The advantages of this system are short reaction times, high yields and the ability to carry out large scale reactions.
- Mirkhani, Valiollah,Moghadam, Majid,Tangestaninejad, Shahram,Kargar, Hadi
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p. 2129 - 2132
(2007/10/03)
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- Microwave-assisted facile synthesis of 2-substituted 2-imidazolines
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A novel method for the synthesis of 2-substituted 2-imidazolines under microwave irradiation is reported. The yields of product obtained using this protocol are significantly high and the reaction time is reduced. ARKAT.
- Pathan, Mohsin Y.,Paike, Vijaykumar V.,Pachmase, Pandurang R.,More, Sandeep P.,Ardhapure, Suresh S.,Pawar, Rajendra P.
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p. 205 - 210
(2013/09/12)
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- An efficient preparation of 2-imidazolines and imidazoles from aldehydes with molecular iodine and (diacetoxyiodo)benzene
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2-Imidazolines were easily prepared in quite good yields from the reaction of aldehydes and ethylenediamine with molecular iodine in the presence of potassium carbonate. Moreover, 2-imidazolines obtained were smoothly oxidized to the corresponding imidazoles in good yields using (diacetoxyiodo)benzene at room temperature. Georg Thieme Verlag Stuttgart.
- Ishihara, Midori,Togo, Hideo
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p. 227 - 230
(2007/10/03)
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- An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water
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The system, I2/KI/K2CO3/H2O, oxidizes carbon-nitrogen bonds for the synthesis of imidazolines and benzimidazoles from aldehydes and diamines under anaerobic conditions in water at 90°C with excellent yields. The process is green, mild and inexpensive.
- Gogoi, Pranjal,Konwar, Dilip
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- A mild and efficient one-pot synthesis of 2-dihydroimidazoles from aldehydes
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The reactions of various aldehydes and 1,2-diamines followed by NXS treatment proceed at 0°C-rt to give the corresponding dihydroimidazoles in high yields. The reaction is mild, and many functional groups such as halogens, nitriles, and esters can exist.
- Fujioka, Hiromichi,Murai, Kenichi,Ohba, Yusuke,Hiramatsu, Atsushi,Kita, Yasuyuki
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p. 2197 - 2199
(2007/10/03)
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- Zeolite-catalyzed simple synthesis of different heterocyclic rings, part 2
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A simple and environmentally friendly synthesis was developed for the preparation of 2-arylimidazoline derivatives and 2-arylbenzoxazole derivatives using a small pore size zeolite. The similar reaction was not applicable to the preparation of the sulfur-containing analogs cysteamine or 2-aminothiophenol, probably because of a disadvantageous reaction between the zeolite and the thio compound.
- Hegedues, Adrienn,Vigh, Ilona,Hell, Zoltan
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p. 428 - 431
(2007/10/03)
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- Reactions of 2,3-diaryl-1-methyl-4,5-dihydroimidazolium iodides with nucleophilic reagents
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2,3-Diaryl imidazolium salts, represented by 1 and 2, reacted with 2-ethanolamine or ethylenediamine to produce 2-aryl oxazolines or imidazolines 5-8 respectively. Their hydrolysis resulted in ring-opened ethylenediamine derivatives 9 and 10. The reduction of 1 and 2 produced partially reduced imidazolidines 11, 12 and 11 reacted further with tryptamine to provide 2,3,4,9-tetrahydro-1-phenyl 1H-pyrido[3,4-b]indole, 13. In all these reactions one-carbon units were successfully transferred to the nucleophilic acceptors, which mimic the one-carbon unit transfer function for tetrahydrofolate coenzymes.
- Xia, Chizhong,Hao, Junsheng,Tang, Yiqing,Ni, Yanping,Zhou, Peiwen
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p. 1457 - 1464
(2007/10/03)
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