- The third-order NLO properties of D-π-A molecules with changing a primary amino group into pyrrole
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The nonlinear refractive index, as well as the two-photon absorption (TPA), has been investigated by the femto-second Z-scan method for push-pull molecules, in which a primary donor group is weakened by conversion into a pyrrole or related heterocycle. The results at the fast response time show that, contrary to what had been expected from a previous work, there is a little decrease in the nonlinear refractive index change by introduction of the weaker donor groups. Although the measured TPA spectra showed that the observed nonlinear refractive index change was regarded to be off-resonant; difference in the frequency dispersion among the molecules considerably contributes to the decrease, in addition to difference in the intrinsic static nonlinearity. This shows that there is some future in the development of these non-resonant materials.
- Audebert,Kamada,Matsunaga,Ohta
-
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Read Online
- A solvent-free manganese(II) -catalyzed Clauson-Kaas protocol for the synthesis of N-aryl pyrroles under microwave irradiation
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The first manganese-catalyzed modified Clauson-Kaas reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction time (20?min). The above qualities attest to the green nature of this reaction.
- Anilkumar, Gopinathan,Meera, Gopinadh,Rohit, Kizhakkekuttu Radhakrishnan
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supporting information
(2021/10/12)
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- Sulphonic acid functionalized porphyrin anchored with a: Meso -substituted triazolium ionic liquid moiety: A heterogeneous photo-catalyst for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation
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We report an easy process to synthesize sulphonic acid functionalized porphyrin, anchored with a meso-substituted triazolium ionic liquid moiety (SAFPTILM) for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation. The acid strength has been measured based on the Hammett indicator. The SAFPTILM photocatalyst comprising 18 π-conjugated electronic systems with the chromophore substituents in the meso-position can provide rapid electronic conducting channels during photocatalysis under the irradiation of visible light. It was found that SAFPTILM is an efficient photocatalyst for the Heck, Sonogashira, Buchwald, Ullmann/Fittig coupling and C-H activation of phenols with different aryl chlorides in the absence of a base/noble metal, using 5 W LED (yellow) light under ambient conditions. The photocatalyst with low band gap (1.55 eV) comprising conjugation, favors coupling reaction of unactivated aryl chlorides, by easy excitation of electrons and transfer to the conjugated benzimidazolium based phenylenediamine support delaying the recombination of photoinduced electron-hole pairs.
- Bhansali, Karan,Raut, Subodh,Barange, Shital,Bhagat, Pundlik
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p. 19690 - 19712
(2020/12/04)
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- Novel substituted benzoyl compound and its pharmaceutically acceptable salt and preparation method and application (by machine translation)
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The invention relates to the general formula I shown novel substituted benzoyl compound and its pharmaceutically acceptable salt and preparation method and application. The invention also provides pharmaceutical compositions containing them, in vitro and in vivo anti-tumor effect results and acute toxicity study, the obtained anti-tumor drug model substituted benzoyl compound, has more excellent anti-tumor activity and safety, can be in the treatment of leukemia, lung cancer, colon cancer, ovarian cancer and renal carcinoma tumor in the application, so that the therapeutic window, so in the medical field as antitumor agents in the very application value. (by machine translation)
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Paragraph 0045; 0048; 0054-0055
(2019/11/13)
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- A facile synthesis of 1-aryl pyrroles by clauson-Kaas reaction using oxone as a catalyst under microwave irradiation
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A new and efficient methodology to synthesize N-substituted pyrrole derivatives by Clauson Kaas reaction employing Oxone as catalyst was developed. The transformation was performed in acetonitrile under microwave irradiation. This procedure has several advantages such as high yield, clean product formation, and short reaction time.
- Gullapelli, Kumaraswamy,Brahmeshwari,Ravichander
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p. 143 - 148
(2019/03/21)
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- Solvent Free Synthesis of N-Substituted Pyrroles Catalyzed by Calcium Nitrate
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Moderated and mild way for synthesizing N-substituted pyrrole has been demonstrated herein. No solvents need to be used for this reaction, and instead, reactants themselves acted as a reaction medium. In fact, the reaction is carried out using catalytic amount of Ca(NO3)2.4H2O. The reaction conditions are selective and mild that helped to tolerate a wide variety of functional groups to give the desired products in good chemical yields.
- Wani, Rucha R.,Chaudhari, Hemchandra K.,Takale, Balaram S.
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supporting information
p. 1337 - 1340
(2019/02/05)
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- Purpurine derivative electrochromic material and preparation method thereof
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The invention discloses a purpurine derivative electrochromic material and a preparation method thereof. The preparation method comprises the steps that 4,4'-dipyridine is adopted as a raw material and undergoes a Menschutkin reaction with 1-chloro-2,4-di
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Paragraph 0008; 0055-0059; 0080-0084
(2019/10/01)
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- Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation
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In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.
- Chen, Fengyang,Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Zhou, Qifan
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p. 4590 - 4600
(2019/12/11)
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- L -(-) -Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles
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l-(-)-Quebrachitol (QCT) has been found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.
- Zhou, Qifan,Du, Fangyu,Chen, Yuanguang,Fu, Yang,Sun, Wenjiao,Wu, Ying,Chen, Guoliang
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p. 8160 - 8167
(2019/06/28)
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- Ultrafine hybrid Cu2O-Fe2O3 nanoparticles stabilized by hexaphenylbenzene-based supramolecular assemblies: A photocatalytic system for the Ullmann-Goldberg coupling reaction
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Ultrafine hybrid Cu2O-Fe2O3 NPs have been prepared using the supramolecular assemblies of hexaphenylbenzene (HPB) derivative 3 as nanoreactors and stabilizers. The as-prepared hybrid Cu2O-Fe2O3 NPs serve as an efficient and recyclable photocatalytic system for carrying out C-N coupling between aryl halides and various amines (aliphatic, aromatic and N-heterocyclic) at room temperature in mixed aqueous media under visible light irradiation. Amazingly, Cu2O-Fe2O3 NPs also exhibited high efficiency in the reactions involving the synthesis of biologically important N-substituted carbazole derivatives. The work being presented in this article demonstrates the preparation of a 'dip strip' coated with the as-prepared catalytic system and utilization of this paper strip as a recyclable and portable heterocatalytic system for carrying out the Ullmann-Goldberg coupling.
- Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
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p. 5346 - 5357
(2018/12/05)
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- Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis
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The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.
- Garnier, Tony,Danel, Mathieu,Magné, Valentin,Pujol, Anthony,Bénéteau, Valérie,Pale, Patrick,Chassaing, Stefan
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p. 6408 - 6422
(2018/05/31)
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- Base-promoted nucleophilic fluoroarenes substitution of C–F bonds
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With the use of KOH/DMSO as the superbase medium, the nucleophilic fluoroarene substitution for C–F bonds is presented. The transformation proceeds smoothly with the use of fluoroarenes bearing not only electron-withdrawing group, but also electron-donating group and a variety of nucleophiles such as alcohols, phenols, amines, amides and nitrogen-heterocyclic compounds. The double nucleophilic substitution using ortho-difluoroarenes and nucleophiles bearing ortho-dinucleophilic groups results in the formation of 2,3-dihydro-1,4-benzodioxins, dibenzo[b,e][1,4]dioxins and 10H-phenoxazines in moderate to good yields.
- Su, Ji,Chen, Qian,Lu, Le,Ma, Yuan,Auyoung, George Hong Lok,Hua, Ruimao
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supporting information
p. 303 - 307
(2017/12/11)
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- Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles
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A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis-aromatization sequence.
- Scalacci, Nicoló,Black, Gary W.,Mattedi, Giulio,Brown, Nicola L.,Turner, Nicholas J.,Castagnolo, Daniele
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p. 1295 - 1300
(2017/08/09)
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- CopperII phthalocyanine as an efficient and reusable catalyst for the N-arylation of nitrogen containing heterocycles
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Copper phthalocyanine (CuIIPc) was found to be an efficient catalyst for the catalyzed N-arylation of N–H heterocycles with aryl iodides and bromides under mild reaction conditions. A variety of hindered and functionalized N–H heterocycles and aryl halides were successfully used as the substrates for the given catalytic reaction and were transformed in good to excellent yields.
- Yadav, Kumar Karitkey,Narang, Uma,Bhattacharya, Soumee,Chauhan, Shive M.S.
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supporting information
p. 3044 - 3048
(2017/07/17)
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- Novel 6-methoxycarbonyl indolinones bearing a pyrrole Mannich base moiety as angiokinase inhibitors
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Inhibition of tumor angiogenesis through simultaneously disturbing vascular endothelial growth factor (VEGF) and platelet-derived growth factor (PDGF) mediated signaling pathways is a well-established approach in intervention of tumor. A series of 6-methoxycarbonyl indolinones bearing a pyrrole Mannich base moiety were synthesized and evaluated as potent angiokinase inhibitors. Compound 8a demonstrated favorable enzymatic activity against all subtypes of VEGFR and PDGFR. Also, it potently suppressed proliferation of HT-29 cells by inducing apoptosis. Compound 8a has emerged as a promising lead compound for development of angiokinase inhibitors targeting VEGFR and PDGFR.
- Qin, Mingze,Yan, Shuang,Wang, Lei,Zhang, Haotian,Tian, Ye,Zhao, Yanfang,Gong, Ping
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p. 1778 - 1786
(2017/03/08)
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- Substituted indolinone derivative and application thereof
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The invention relates to a substituted indolinone derivative represented as the general formula (I) and used as a tyrosine kinase inhibitor, and medicinal acceptable salts or isomers thereof, wherein the R1, R2, R3, R4, R5, R6, R7, n and the ring A are defined as the specifications. The invention also relates to a preparation method of the compound, and an application of the compound in preparation of medicines for prevention or therapy of fibrosis diseases and excess hyperplasia diseases.
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Paragraph 0117; 0119; 0120; 0121
(2017/08/02)
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- A carbon nitride supported copper nanoparticle composite: a heterogeneous catalyst for the N-arylation of hetero-aromatic compounds
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A graphitic carbon nitride supported copper nanoparticle composite (Cu-gCN) has been found to be an active catalyst for the N-arylation of hetero-aromatic systems (pyrrole, pyrazole, and substituted indole) and benzamide molecules, with high product selectivity and good to excellent yields, using substituted aryl bromide as a coupling partner. The intercalated structure and the amine functional group of the carbon nitride prevent the aggregation of the catalytically active copper species during the reaction, and the recyclability study shows the stable performance of the catalyst without a significant loss of catalytic activity.
- Nandi, Debkumar,Siwal, Samarjeet,Mallick, Kaushik
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supporting information
p. 3082 - 3088
(2017/04/14)
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- N-Picolinamides as ligands for Ullmann-type C-N coupling reactions
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The use of N-phenyl-2-pyridincarboxamide-1-oxide as a ligand with Cu2O in Ullmann type C-N bond formations between aryl halides and N-heteroaryls in common solvents, such as MeCN, DMF, and DMSO at 82-120 °C has been successfully demonstrated. The ligand is effective when only 4% equiv is used relative to the substrate. The reaction provided the corresponding products in coupling of electron-rich, electron poor, and ortho-substituted aryl halides, including ortho aryl-chlorides, in good to very good yields. N-arylation is selectively preferred at the benzyl position when ortho-halide benzyl bromide is reacted with one equivalent of pyrazole. However, di-N-arylation is achieved in very high yields when 2.5 equiv of pyrazole is used, providing a stoichiometric control over the coupling reaction.
- Damkaci, Fehmi,Alawaed, Abdulkhaliq,Vik, Erik
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supporting information
p. 2197 - 2200
(2016/05/02)
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- Electronically Strongly Coupled Divinylheterocyclic-Bridged Diruthenium Complexes
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Complexes [{Ru(CO)Cl(PiPr3)2}2(μ-2,5-(CH=CH)2-cC4H2E] (E=NR; R=C6H4-4-NMe2 (10a), C6H4-4-OMe (10b), C6H4-4-Me (10c), C6H5 (10d), C6H4-4-CO2Et (10e), C6H4-4-NO2 (10f), C6H3-3,5-(CF3)2 (10g), CH3 (11); E=O (12), S (13)) are discussed. The solid state structures of four alkynes and two complexes are reported. (Spectro)electrochemical studies show a moderate influence of the nature of the heteroatom and the electron-donating or -withdrawing substituents R in 10a-g on the electrochemical and spectroscopic properties. The CVs display two consecutive one-electron redox events with ΔE°′=350-495 mV. A linear relationship between ΔE°′ and the σp Hammett constant for 10a-f was found. IR, UV/Vis/NIR and EPR studies for 10+-13+ confirm full charge delocalization over the {Ru}CH=CH-heterocycle-CH=CH{Ru} backbone, classifying them as Class III systems according to the Robin and Day classification. DFT-optimized structures of the neutral complexes agree well with the experimental ones and provide insight into the structural consequences of stepwise oxidations.
- Pfaff, Ulrike,Hildebrandt, Alexander,Korb, Marcus,O?wald, Steffen,Linseis, Michael,Schreiter, Katja,Spange, Stefan,Winter, Rainer F.,Lang, Heinrich
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p. 783 - 801
(2016/01/15)
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- Carbon nitride supported palladium nanoparticles: An active system for the reduction of aromatic nitro-compounds
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Synthesis of carbon nitride supported highly dispersed ultrafine palladium nanoparticles has been reported for the reduction of aromatic nitro-compounds using hydrazine hydrate as a reducing agent. As a demonstration, the as-synthesized carbon nitride-palladium composite was shown to be a highly active and chemo-selective for the title reaction. Utilizing the optimized reaction conditions a set of aromatic nitro compounds have been converted to their corresponding amine derivatives with good to excellent yield ranging from 80% to 99%. The catalyst can be used for multiple times without affecting the catalytic performance and can also be stored for a long time at ambient condition maintaining the high catalytic efficiency.
- Nandi, Debkumar,Siwal, Samarjeet,Choudhary, Meenakshi,Mallick, Kaushik
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- An efficient heterogeneous catalytic method for the N-arylation of pyrrole and other N-heterocycles
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Abstract 4 ? molecular sieve modified with copper(0) or copper(II) is an efficient heterogeneous catalyst for the arylation of pyrrole and some other heterocycles with iodo- or bromoarenes, Cs2CO3 base and pyrrole (or DMF) solvent. The catalysts can be easily prepared and are reusable.
- Nmeth, Jnos,Debreczeni, Nra,Gresits, Ivn,Blint, Mria,Hell, Zoltn
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p. 1113 - 1119
(2015/08/06)
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- Functionalized multi-walled carbon nanotubes as an efficient reusable heterogeneous catalyst for green synthesis of N-substituted pyrroles in water
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In this protocol, the functionalization of multi-walled carbon nanotubes (MWCNTs) was carried out and the resulting sulfonated MWCNTs were characterized by FT-IR, XRD, SEM, BET, EDX, XPS and Raman spectroscopy that are each discussed separately in the text. Then, the MWCNT-SO3H composite was applied as an efficient, recyclable heterogeneous catalyst for the synthesis of N-substituted pyrroles via the reaction of 2,5-dimethoxy tetrahydrofuran with primary amines under clean and mild conditions. In this reaction, the N-substituted pyrroles were obtained as beneficial and significant products in short reaction times (30-65 min) and good to excellent yields (40-92%) with high purity. The products were obtained through a simple work up procedure and characterized by FT-IR, 1H NMR and 13C NMR. After the end of the reaction, the nanocatalyst was recovered and reused several times without efficient loss of its activity for the preparation of N-substituted pyrroles.
- Naeimi, Hossein,Dadaei, Mahla
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p. 76221 - 76228
(2015/09/28)
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- Design, synthesis and structure - activity relationship of oxazolidinone derivatives containing novel S4 ligand as FXa inhibitors
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Abstract A novel series of potent and efficacious factor Xa inhibitors which possesses pyrrole/indole/thiazole moieties as S4 binding element was identified. Compound 7b showed strong human factor Xa inhibitory activity (IC50 = 2.01 nM) and ant
- Zhao, Yanfang,Jiang, Mingyan,Zhou, Shunguang,Wu, Shasha,Zhang, Xiaolong,Ma, Longsheng,Zhang, Kai,Gong, Ping
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p. 369 - 380
(2015/05/05)
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- An elegant protocol for the synthesis of N-substituted pyrroles through C-N cross coupling/aromatization process using CuFe2O4 nanoparticles as catalyst under ligand-free conditions
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A simple and efficient, ligand-free C-N cross-coupling of aryl halides/benzyl bromides with trans-4-hydroxy-l-proline has been developed to produce aromatized N-substituted pyrroles, using a catalytic amount of magnetically separable and recyclable CuFe2O4 nanoparticles, in the presence of Cs2CO3 in DMSO at 100 °C.
- Satish,Reddy, K. Harsha Vardhan,Ramesh,Kumar, B.S.P. Anil,Nageswar
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supporting information
p. 2596 - 2599
(2014/05/06)
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- Highly active recyclable heterogeneous Pd/ZnO nanoparticle catalyst: Sustainable developments for the C-O and C-N bond cross-coupling reactions of aryl halides under ligand-free conditions
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Efficient Pd supported on ZnO nanoparticles for the ligand-free O-arylation and N-arylation of phenols and various N-H heterocycles with aryl chlorides, bromides, and iodides were readily synthesized and characterized. The amount of palladium on ZnO is 9.84 wt% (0.005 g of the catalyst contains 462 × 10-8 mol% of Pd) which was determined by ICP analysis. This nano sized Pd/ZnO with an average particle size of 20-25 nm and specific surface area 40.61 m2 g-1 was used as a new reusable heterogeneous catalyst for the formation of C-O and C-N bonds in organic synthesis. This protocol gives the arylated product in satisfactory yields without any N2 or Ar flow. The catalyst can be recovered and recycled several times without marked loss of activity.
- Hosseini-Sarvari, Mona,Razmi, Zahra
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p. 44105 - 44116
(2014/12/10)
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- L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
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l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.
- Wang, Ping,Ma, Fei-Ping,Zhang, Zhan-Hui
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p. 259 - 262
(2014/11/07)
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- Synthesis of pyrrole derivatives from diallylamines by one-pot tandem ring-closing metathesis and metal-catalyzed oxidative dehydrogenation
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A series of aryl-substituted pyrrole derivatives was synthesized from diallylamines through a ruthenium carbene catalyzed ring-closing metathesis reaction and in situ oxidative dehydrogenation reaction catalyzed by FeCl 3·6H2O or CuCl2·2H2O in the presence of O2. The reaction was mild, simple, and convenient. An oxygen atmosphere played a critical role in obtaining high conversion of substituted pyrroles in the proposed catalytic system.
- Chen, Weiqiang,Wang, Jianhui
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supporting information
p. 1958 - 1963
(2013/05/08)
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- Copper MOF: Scope and limitation in catalytic hydroxylation and nitration of aryl halides
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The potential catalytic application of MOFs like [Cu3(btc) 2] (btc=1,3,5-benzenetricarboxylate), [Cu(bdc)] (bdc=1,4- benzenedicarboxylate), [Cu(pymo)2] (pymo=2-hydroxypyrimidinalote) and [Cu(im)2] (im=imidazolate) was explored in the hydroxylation and nitration of aryl halides. Cu3(btc)2 was found to be superior for both the reactions furnishing good to excellent yields of the respective products. The studies demonstrated that MOFs are not recyclable, attributable to their instability in the highly polar and basic conditions demanded for these reactions. Complete transformation of MOFs to copper oxide nanoparticles occurred in hydroxylation, whereas significant alteration in frameworks was observed for the recovered catalyst in nitration.
- Priyadarshini,Amal Joseph,Kantam, M. Lakshmi,Sreedhar
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p. 6409 - 6414
(2013/07/26)
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- Facial preparation of sulfonic acid-functionalized magnetite-coated maghemite as a magnetically separable catalyst for pyrrole synthesis
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The synthesis, characterization, an Copyright
- Mahmoudi, Hajar,Jafari, Abbas Ali
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p. 3743 - 3749
(2014/01/06)
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- Synthesis of heteroaromatic derivatives with nitrogen atoms: Tripyrrolyl pyrimidine and tripyrrolyl[1,3,5]triazine
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As a part of a research program related to the synthetic study of pharmacologically and photoconductively interesting pyrrole derivatives, we have synthesized 1-arylpyrroles (3a-e), 9-arylcarbazoles (4a-e), aminophenylpyrroles (6a,b), dipyrrolylbenzenes (7a-c), 2,4,6-tri-pyrrol-1- yl-pyrimidine (8) and 2,4,6-tri-pyrrol-1-yl[1,3,5]triazine (9). We proposed a plausible mechanism for the formation of 9-arylcarbazole.
- Lee,Lee,Jung,Hahn
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p. 501 - 504
(2013/02/22)
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- Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media
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An operationally simple and efficient protocol for squaric acid catalyzed synthesis of N-substituted pyrroles via the reaction of 2,5- dimethoxytetrahydrofuran and 2,5-hexandione with aryl amines in green reaction media (water, deep eutectic solvent, and polyethylene glycol) under ultrasound irradiation or thermal conditions in good to excellent yields has been developed.
- Azizi, Najmadin,Davoudpour, Anahita,Eskandari, Farshid,Batebi, Ehlham
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p. 405 - 409
(2013/05/09)
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- A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water
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A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.
- Ma, Fei-Ping,Li, Pei-He,Li, Bao-Le,Mo, Li-Ping,Liu, Ning,Kang, Hui-Jun,Liu, Ya-Nan,Zhang, Zhan-Hui
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- Copper catalyzed ipso-nitration of iodoarenes, bromoarenes and heterocyclic haloarenes under ligand-free conditions
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A catalytic protocol for the conversion of haloarenes into the corresponding nitroarenes is presented using copper salts under ligand-free conditions. The method was effectively utilized for the ipso-nitration of a broad variety of haloarenes that includes iodoarenes, bromoarenes, and heterocyclic haloarenes.
- Amal Joseph,Priyadarshini,Lakshmi Kantam,Maheswaran
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supporting information; experimental part
p. 1511 - 1513
(2012/03/27)
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- Novel approach for the synthesis of N-Substituted pyrroles starting directly from nitro compounds in water
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A novel approach for a facile high-yielding synthesis of N-substituted pyrroles has been discovered by the treatment of nitroarenes with 2,5-dimethoxytetrahydrofuran using indium in dilute aqueous HCl at room temperature. Taylor & Francis Group, LLC.
- Das, Biswanath,Shinde, Digambar Balaji,Kanth, Boddu Shashi,Kumar, Jayprakash Narayan
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p. 548 - 553
(2011/11/29)
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- Synthesis of N-substituted pyrroles under catalyst-and solvent-free conditions
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N-Substituted pyrroles were synthesized under neat conditions by the reaction of aromatic amines with 2, 5-dimethoxytetrahydrofuran in excellent yields.
- Ramesh, Katla,Murthy, Sabbavarapu Narayana,Nageswar, Yadavalli Venkata Durga
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experimental part
p. 2471 - 2477
(2012/06/29)
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- New strategy for the synthesis of N-aryl pyrroles: Cu-catalyzed C-N cross-coupling reaction of trans-4-hydroxy-l-proline with aryl halides
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trans-4-Hydroxy-l-proline is used for the first time as an effective nucleophilic coupling partner with aryl halides mediated by copper iodide with Cs2CO3 as the base and DMSO as the solvent. Utilizing this protocol cross-coupling of trans-4-hydroxy-l-proline with a wide variety of substituted aryl halides to produce N-aryl pyrroles in moderate to good yields.
- Reddy, V. Prakash,Kumar, A. Vijay,Rao, K. Rama
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experimental part
p. 777 - 780
(2011/03/21)
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- Tungstophosphoric acid supported on silica gel (H3PW 12O40/SiO2) as an eco-friendly, reusable and heterogeneous catalyst for the synthesis of pyrroles in solution or under solvent-free microwave irradiation
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Heteropoly acid supported on silica gel (H3PW12O 40/SiO2) is easily used as a heterogonous, reusable and efficient catalyst for the synthesis of N-substituted, 2- and 3-unsubstituted pyrroles in solution or under solvent-free microwave irradiation. The catalyst can be easily recovered and reused for several times without loss of activity.
- Jafari,Mahmoudi,Mirjalili
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experimental part
p. 851 - 856
(2012/06/18)
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- Unique chemoselective Clauson-Kass reaction of substituted aniline catalyzed by MgI2 etherate
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Clauson-Kass reaction of various substituted aniline, primary aryl amide, and sufonyl amide with 2,5-dimethoxytetrahydrofuran was realized in the presence of 10 mol % of MgI2 etherate in a mild, efficient, and highly chemoselective manner. Iodide counterion and solvents (i.e., MeCN) played the critical roles for the unique reactivity of this catalytic system.
- Zhang, Xingxian,Shi, Junchen
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experimental part
p. 898 - 903
(2011/03/19)
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- Two Component Recyclable Heterogeneous Catalyst, Process for Preparation Thereof and its Use for Preparation of Amines
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The invention describes the development of highly efficient, recyclable two component system, CuAl-hydrotalcite/rac 1,1′-Binaphthalene-2,2′-diol catalytic system for the N-alkylation of electron deficient aryl chlorides in presence of potassium carbonate as a base at room temperature in 3-6 h, wherein the process is provided for the preparation of various secondary amines via C—N coupling reaction of aliphatic amines(aliphatic open chain, acyclic, benzyl amines and heterocyclic amines) with various aryl chlorides.
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Page/Page column 8
(2012/01/13)
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- Nano ceria catalyzed Ullmann type coupling reactions
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Ullmann type intermolecular coupling of aryl halide with hetero-aromatic compounds, such as phenols, amines, and thiophenols are key reactions for the formation of carbon-heteroatom bond in organic synthesis. We report a robust and novel method that provides an efficient and economic route for the synthesis of O, N, and S-arylation via Ullman coupling by using nano cerium oxide (ceria, CeO2). CeO2 is a cheaper catalyst compared to related copper based catalysts. This method provides a wide range of substrate applicability in the case of phenols and amines. Less reactive chlorobenzene substituted with strong electron withdrawing groups such as 4-nitrochlorobenzene and 4-cyanochlorobenzene favor the reaction. This protocol avoids the use of ligand and gives arylated product in satisfactory yields.
- Agawane, Sandeep M.,Nagarkar, Jayashree M.
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experimental part
p. 5220 - 5223
(2011/10/12)
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- Copper ferrite nanoparticle-mediated N-arylation of heterocycles: A ligand-free reaction
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The synergistic effects of iron and copper in copper ferrite nanoparticles for the N-arylation of heterocycles with aryl halides were demonstrated. The magnetic nature of the catalyst facilitates its removal from the reaction medium for further use. Negligible leaching of Cu and Fe in consecutive cycles makes the catalyst economical and environmentally benign for C-N cross-coupling reactions.
- Panda, Niranjan,Jena, Ashis Kumar,Mohapatra, Sasmita,Rout, Smruti Ranjan
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supporting information; experimental part
p. 1924 - 1927
(2011/04/25)
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- Ligand-free CuCl-catalyzed C-N bond formation in aqueous media
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CuCl-catalyzed N-arylation of alkyl amines and N-heterocycles with substituted aryl iodides and bromides can be carried out in 40% nBu4N+OH- aqueous solution without any ligands. Crown Copyright
- Xu, Hua-Jian,Zheng, Fa-Yin,Liang, Yu-Feng,Cai, Zhen-Ya,Feng, Yi-Si,Che, Da-Qing
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experimental part
p. 669 - 671
(2010/04/23)
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- C-N bond formation catalysed by CuI Bonded to polyaniline nanofiber
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Polyaniline nanofiber as a macroligand for the supported cuprous iodide catalyst (CuI-PANInf) has been developed for the coupling of aryl halides (including aryl chlorides) with aliphatic, aromatic, and N(H)-heterocyclic amines under ambient conditions (80 °C for aryl chlorides) has been developed. This simple and efficient method for coupling reactions is highly versatile, convenient, and also the catalyst can be used for several cycles with good-to-excellent yields.
- Arundhathi, Racha,Kumar, Desitti Chaitanya,Sreedhar, Bojja
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supporting information; experimental part
p. 3621 - 3630
(2010/08/20)
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- Oxazolidin-2-one as efficient ligand for the copper-catalyzed N- Arylation of pyrrole, imidazole and indole
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Oxazolidin-2-one was found to be a facile ligand for the N-arylation of pyrrole, indole, and imidazole with aryl and heteroaryl iodides, bromides, and chlorides by applying Cul as catalyst. The easy preparation, commercial availability, lower molecular weight, and broad substrate applicability, as well as substituent compatibility of this catalysis system render oxazolidin-2-one great advantages over the Cu-catalyzed methods that have already been utilized in a number of applications.
- Ma, Hengchang,Wu, Shang,Sun, Qiangsheng,Lei, Ziqiang
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experimental part
p. 212 - 218
(2011/07/07)
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- CuCl-catalyzed formation of C-N bond with a soluble base
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Tetramethylammonium hydroxide was used as a base instead of a traditional inorganic base in this copper-catalyzed system and some satisfactory results were obtained. Various functional groups were compatible under this reaction condition.
- Feng, Yi-Si,Man, Qiu-Shi,Pan, Pan,Pan, Zong-Qin,Xu, Hua-Jian
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experimental part
p. 2585 - 2588
(2009/08/07)
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- Iron-catalyzed inexpensive and practical synthesis of N-substituted pyrroles in water
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An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions. Georg Thieme Verlag Stuttgart.
- Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad,Saidi, Mohammad Reza
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experimental part
p. 2245 - 2248
(2009/12/03)
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- Scandium triflate-catalysed synthesis of N-substituted pyrroles from amine and 2,5-dimethoxytetrahydrofuran
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The Clauson-Kass pyrrole synthesis catalysed by scandium triflate afforded N-substituted 2- and 3-unsubstituted pyrroles with yields ranged from good to excellent. Aromatic amines, heteroaomatic amines, 4-methylbenzenesulfonamide and 2-chlorobenzamide are good substrates in this transformation.
- Zuo, Bing,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue,Su, Weike
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experimental part
p. 14 - 16
(2009/09/25)
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- Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics
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(Chemical Equation Presented) An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent
- Fors, Brett P.,Buchwald, Stephen L.
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supporting information; experimental part
p. 12898 - 12899
(2009/12/07)
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- Highly practical "ligand-free-like" copper-catalyzed N-arylation of azoles in lower nitrile solvents
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In lower nitrile solvents, the N-arylation of azoles with aryl halides was achieved efficiently in the presence of copper powder without any additional ligands. Thus, the first nitrile type of monodentate ligand-mediated, "ligand-free-like" copper-catalyzed N-arylation procedure was established.
- Zhu, Rui,Xing, Lixin,Wang, Xinyan,Cheng, Chuanjie,Su, Deyong,Hu, Yuefei
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supporting information; experimental part
p. 1253 - 1257
(2009/06/18)
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- N-arylation of heterocycles with chloro- and fluoroarenes using resin-supported sulfonato-Cu(salen) complex
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Sulfonato-Cu(salen) complex immobilized onto a Merrifield's resin was found to be an efficient catalyst for the N-arylation of heterocycles with electron-withdrawing hloro- and fluoroarenes. The reactions were carried out in the presence of an inexpensive mild base, K2CO3, and N-arylated compounds were obtained in good to excellent yields. The catalyst was recovered by simple filtration and reused for three cycles with almost consistent activity. Copyright Taylor & Francis Group, LLC.
- Kantam, M. Lakshmi,Ramani,Chakrapani
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p. 626 - 636
(2008/04/12)
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- Synthesis of (1H-pyrrol-2-ylsulfanyl)alkanoic acids
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(1-Benzyl-1H-pyrrol-2-ylsulfanyl)acetic acid, 2- and 3-(1-benzyl-1H-pyrrol- 2-ylsulfanyl)propionic acids, 1,1′-[1,4-phenylenebis(methylene)]bis[(1H- pyrrol-2-ylsulfanyl)acetic acid], and 1,1′-(hexane-1,6-diyl)bis-[(1H- pyrrol-2-ylsulfanyl)acetic acid] were synthesized for the first time by reactions of 1-benzyl-1H-pyrrole, 1,1′-[1,4-phenylenebis(methylene)] bis(1H-pyrrole), and 1,1′-(hexane-1,6-diyl)bis(1H-pyrrole) with thiourea, iodine, and the corresponding halogen-substituted alkanoic acids. 1-(4-Nitrophenyl)-1H-pyrrole failed to react with thiourea and iodine.
- Rudyakova,Mirskova,Levkovskaya
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experimental part
p. 1517 - 1521
(2009/06/21)
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