- Synthesis of (fluoroalkyl)amines by deoxyfluorination of amino alcohols
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Deoxyfluorination of amino alcohols was achieved using N,N-diethyl-α, α-difluorobenzylamine (DFBA) to furnish N-benzoyl(fluoroalkyl)amines selectively. Georg Thieme Verlag Stuttgart.
- Nomoto, Takashi,Fukuhara, Tsuyoshi,Hara, Shoji
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Read Online
- Synthesis of organochalcogens stabilized by intramolecular non-bonded interactions of sterically unhindered 2-phenyl-2-oxazoline
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The synthesis and characterization of low-valent organoselenium and -sulfur compounds incorporating sterically unhindered 2-phenyl-2-oxazoline are described. Organylselenenyl halides, RSeX (X = Cl, Br, I) were prepared from diselenide and the benzyl selenide derivative was synthesized by the reaction of in situ generated lithium arylselenolate, OxSe-Li+ (Ox = 2-phenyl-2-oxazoline) with benzyl chloride. These compounds in general show strong Se...N intramolecular interactions as compared with the substituted oxazoline analogues. Bis[2-(2-oxazolinylphenyl)] disulfide and [2-(2-oxazolinyl)phenyl]benzyl sulfide were synthesized by the ortho-lithiation method and characterized by 1H and 13C NMR spectroscopy. The S...N intramolecular interactions were confirmed by single crystal X-ray crystallography.
- Kumar, Sangit,Kandasamy, Karuppasamy,Singh, Harkesh B.,Butcher, Ray J.
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Read Online
- Facile one-pot synthesis of 2-oxazoline
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We developed a facile one-pot synthesis of 2-oxazolines from carboxylic acid and 2-chloroethyl isocyanate, involving amide bond formation and a following intramolecular cyclization using 4-dimethylaminopyridine as the catalyst. A large variety of functional groups are well tolerated by the mild reaction conditions to afford diverse 2-oxazolines in good to excellent yields. This reaction will keep the chirality of the isocyanate at position 1, the R2 substituted carbon. Microwave-assisted synthesis can further enhance the reaction yield and reduce the reaction time to 5 min. This method facilities the synthesis of 2-oxazolines for diverse applications, such as 2-oxazoline derived polymers and materials.
- Jiang, Weinan,Liu, Runhui,Song, Gonghua,Zhou, Min,Zhou, Yang,Zhu, Jipeng
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supporting information
(2022/01/28)
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- Synthesis of Nitrogen-Containing Heterocycles through Catalytic Dehydrative Cyclization Reactions
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Re2O7 in hexafluoroisopropyl alcohol provides access to cationic intermediates from alcohols through the intermediacy of perrhenate esters. This manuscript describes the application of the system to the formation of a number of weakly basic heterocyclic systems through dehydration reactions and intramolecular nucleophilic addition. The influence of the substrate structure on the reaction rates and stereocontrol is discussed with respect to intermediate ion pairs.
- Rodriguez Del Rey, Freddy O.,Floreancig, Paul E.
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supporting information
p. 150 - 154
(2021/01/09)
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- Ultrasound-Accelerated, Concise, and Highly Efficient Synthesis of 2-Oxazoline Derivatives Using Heterogenous Calcium Ferrite Nanoparticles and Their DFT Studies
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A rapid and operationally simple approach for synthesising biologically relevant 2-oxazoline derivatives has been developed through highly efficient ultrasound-promoted coupling reactions of thioamides and amino alcohols using calcium ferrite nanoparticles as heterogeneous catalysts. The major advantage of using ultrasound irradiation lies in the drastic reduction of reaction time as compared with conventional stirring. Furthermore, quantum chemical investigations for the synthesised 2-oxazoline derivatives have been carried out at the DFT/B3LYP/6-311 + G (d, p) level of theory to predict the optimized geometry. The molecular properties such as bond lengths, bond orders, Milliken charges, frontier molecular orbitals, global reactivity descriptors, molecular electrostatic potential map, and thermodynamic parameters of all the compounds have also been reported at the same level of theory.
- Atri, Shalu,Bendi, Anjaneyulu,Rao, G. B. Dharma,Raza, Mohd Jamshaiya,Sharma, Nutan
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- Ruthenium-catalysedmeta-selective CAr-H bond alkylationviaa deaminative strategy
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The use of aliphatic amines as alkylating reagents in organic synthesisviaC-N bond activation remains underdeveloped. We herein describe a novel ruthenium-catalysed and directing-group assisted protocol for the synthesis ofmeta-alkylated arenesviadual C-H and C-N activation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amines and amino acid species were used as alkyl radical precursors. This catalytic reaction could accommodate a broad range of functional groups and provide access to variousmeta-alkylated products.
- Zhu, Ze-Fan,Chen, Guang-Le,Liu, Feng
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supporting information
p. 3411 - 3414
(2021/04/07)
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- Rhodium(III)-Catalyzed Oxidative Cyclization of Oxazolines with Cyclopropanols: Synthesis of Isoindolinones
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The synthesis of C3-substituted isoindolin-1-ones from oxazolines and cyclopropanols has been achieved with oxazoline as a bifunctional nucleophilic directing group. The reaction proceeds by the cleavage of three chemical bonds and allows the formation of three new chemical bonds, a C-N bond, a C-C bond, and a C-O bond, in a single step.
- Liu, Jidan,Yang, Zhenke,Jiang, Jinyuan,Zeng, Qiaohai,Zheng, Liyao,Liu, Zhao-Qing
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supporting information
p. 5927 - 5931
(2021/07/31)
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- Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4 H -1,3-thiazines
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An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4 H -1,3-thiazines is developed via microwave-assisted ring closure of ω-thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an S N 2-type mechanism and features the advantages of very short reaction times, high yields and a predictable stereochemical outcome. The acyclic precursors are prepared in high overall yields by an improved diacylation-thionation-saponification sequence from commercially available ω-amino alcohols. The whole process is metal-free and operationally simple.
- Bisceglia, Juan A.,Kilimciler, Natalia B.,Mancinelli, Michele,Mollo, María C.,Orelli, Liliana R.
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p. 1666 - 1679
(2020/06/01)
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- Catalytic β C-H amination: Via an imidate radical relay
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The first catalytic strategy to harness imidate radicals for C-H functionalization has been developed. This iodine-catalyzed approach enables β C-H amination of alcohols by an imidate-mediated radical relay. In contrast to our first-generation, (super)stoichiometric protocol, this catalytic method enables faster and more efficient reactivity. Furthermore, lower oxidant concentration affords broader functional group tolerance, including alkenes, alkynes, alcohols, carbonyls, and heteroarenes. Mechanistic experiments interrogating the electronic nature of the key 1,5 H-atom transfer event are included, as well as probes for chemo-, regio-, and stereo-selectivity.
- Stateman, Leah M.,Wappes, Ethan A.,Nakafuku, Kohki M.,Edwards, Kara M.,Nagib, David A.
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p. 2693 - 2699
(2019/03/06)
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- Oxazolinyl-Assisted Ru(II)-Catalyzed C-H Allylation with Allyl Alcohols and Synthesis of 4-Methyleneisochroman-1-ones
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We report herein a ruthenium-catalyzed, oxazoline-directed strategy for C-H allylation of aryl oxazolines using allylic alcohols as the coupling partner. The present transformation unravels the unusual reactivity of allylic alcohols in the synthesis of 4-
- Singh, Diksha,Kumar, Gangam Srikanth,Kapur, Manmohan
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p. 12881 - 12892
(2019/09/30)
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- Oxazolinyl-Assisted Ru(II)-Catalyzed C?H Functionalization Based on Carbene Migratory Insertion: A One-Pot Three-Component Cascade Cyclization
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A rare, ruthenium-catalyzed, oxazolinlyl assisted C?H functionalization and three-component cascade cyclization for the synthesis of isoquinolinones via a metal-carbene migratory insertion is reported. The transformation is unique since it involves the fo
- Kumar, Gangam Srikanth,Khot, Nandkishor Prakash,Kapur, Manmohan
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supporting information
p. 73 - 78
(2018/12/11)
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- Benzyne-mediated trichloromethylation of chiral oxazolines
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A three-component reaction between benzyne, oxazolines and chloroform was developed for the synthesis of trichloromethylated chiral oxazolidines. Benzyne not only serves as an electrophile towards oxazolines but also acts as a base for the deprotonation of chloroform. The dual functions of benzyne enable the trichloromethylation of chiral oxazolines and thus construct chiral N,O-quaternary stereocenters.
- Huang, Xin,Zhao, Weizhao,Chen, De-Li,Zhan, Yaling,Zeng, Tingting,Jin, Huiquan,Peng, Bo
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supporting information
p. 2070 - 2073
(2019/02/19)
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- RuO4-mediated oxidation of N-benzylated tertiary amines. Four- And three-membered azacycloalkanes as substrates
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Similarly to N-benzylpiperidine and -pyrrolidine, N-benzylazetidine underwent RuO4-catalyzed oxidation by attack at both types of N-methylene C-H bonds: Endocyclic and exocyclic (benzylic). If the reaction is performed in the presence of cyanide, α-aminon
- Florea, Cristina A.,H?rtopeanu, Anca,Stavarache, Cristina,Petride, Horia
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p. 294 - 307
(2018/11/26)
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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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- Directed β C-H Amination of Alcohols via Radical Relay Chaperones
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A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.
- Wappes, Ethan A.,Nakafuku, Kohki M.,Nagib, David A.
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p. 10204 - 10207
(2017/08/10)
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- A study on reactions of an alkynylsilane with oxone-KX (X = Cl, Br, I) and its one-pot transformation into an amide/ester
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Oxyhalogenation reactions of a variety of alkynylsilanes were studied using oxone as mild oxidant and KCl, KBr, and KI as halogen sources. In this study, reaction of an alkynylsilane with oxone-KX (X = Cl or Br) produced trichloromethyl/tribromomethyl ketones inhigh yields. Under similar conditions, however, reactions of alkynylsilanes with oxone-KI were found to give exclusively 1,2,2-triiodovinyl derivatives in high yields. In this study, new methods were deveoped for effcient one-pot tranformation of alkynylsilanes into amides and esters by reaction with amines and alcohols respectively via trihalomethyl ketone.
- Sriramoju, Vinodkumar,Jillella, Raveendra,Kurva, Srinivas,Madabhushi, Sridhar
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p. 560 - 562
(2017/03/30)
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- A 2 - substituted oxazoline or 2 - substituted piperazine synthetic method (by machine translation)
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The invention discloses a method for synthesizing 2 - substituted oxazoline or 2 - substituted oxazine new method, by nitrile and amino ethanol or 3 - amino - 1 - propanol as raw material, in the absence of solvent, can be used for the recycling of the sulfur to induce synthesis of 2 - substituted oxazoline and 2 - substituted piperazine. The method of the invention has low cost, simple reaction process, mild reaction conditions, the reaction time is short, the yield and the like, is suitable for the industrial generation. (by machine translation)
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Paragraph 0023; 0024; 0033
(2017/08/25)
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- Highly efficient synthesis of β-nitrate ester carboxamides through the ring-opening of 2-oxazolines
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A novel method for the synthesis of β-nitrate ester carboxamides using non-corrosive tert-butyl nitrite (TBN) as the nitro source and easily available oxygen as the oxidant has been developed. Variously substituted 2-oxazolines were efficiently ring-opened to deliver the corresponding products in excellent yields. Notably, this reaction provides fast access to pharmaceuticals such as nicorandil.
- Qiao, Kai,Yuan, Xin,Wan, Li,Zheng, Ming-Wei,Zhang, Dong,Fan, Bing-Bing,Di, Zhe-Chen,Fang, Zheng,Guo, Kai
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supporting information
p. 5789 - 5793
(2017/12/26)
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- A 2 - aryl - 2 - oxazoline preparation method
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The invention discloses a 2-aryl-2-oxazoline preparation method and belongs to the field of chemistry. According to the method, an aryl-amide compound and 1,2-dichloroethane are reacted for synthesis, and the synthesis reaction is conducted under the alka
- -
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Paragraph 0007; 0017; 0018
(2017/06/21)
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- Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines
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The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.
- Mollo, María C.,Orelli, Liliana R.
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supporting information
p. 6116 - 6119
(2016/12/09)
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- Potentiation of the fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida
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A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida. From the screen a highly potent 2-oxazoline adjuvant was discovered capable of potentiating FR 900098 with a 1000-fold reduction in MIC against the Francisella sub-species F. novicida and F. philomiragia.
- Stephens, Matthew D.,Yodsanit, Nisakorn,Melander, Christian
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supporting information
p. 1952 - 1956
(2016/10/22)
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- Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles
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Acidic sulfonimide nucleophiles including dibenzenesulfonimide, o-benzenesulfonimide, dimethanesulfonimide, and N-(methylsulfonyl)-benzenesulfonamide are discovered to open a variety of alkyl-, aryl- and heteroaryl-2-oxazoline rings to provide the sulfonimidation products in refluxing 1,4-dioxane. The electron-rich 2-oxazoline substrates worked well for the nucleophilic ring-opening reactions while no reaction took place for the electron-poor 2-oxazoline substrates.
- Gutierrez, David A.,Dean, Dayton R.,Laxamana, Candace M.,Migliozzi-Smith, Madyson,O'Brien, Connor J.,O'Neill, Claire L.,Li, Jie Jack
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p. 261 - 276
(2016/07/06)
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- Willgerodt–Kindler reaction-driven one pot solventless entry to 2-oxazolines
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We report an efficient and green protocol for the synthesis of 2-oxazolines by the reaction of aromatic nitriles with β-aminoalcohols using sulfur under solvent-free conditions. The reaction occurs via the Willgerodt-Kindler mechanism followed by transami
- Bansal, Shivani,Gupta, Poonam,Halve
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p. 971 - 974
(2016/07/06)
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- Copper N-Heterocyclic Carbene Complexes As Active Catalysts for the Synthesis of 2-Substituted Oxazolines from Nitriles and Aminoalcohols
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The reaction between nitriles and aminoalcohols to access 2-substituted oxazolines was investigated. Using copper-NHC complexes, various nitriles were successfully converted into the corresponding oxazolines, under milder and less wasteful conditions than those of previously reported methods.
- Trose, Michael,Lazreg, Fa?ma,Lesieur, Mathieu,Cazin, Catherine S. J.
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p. 9910 - 9914
(2015/11/03)
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- Ruthenium(II) 9,10-phenanthrenequinone thiosemicarbazone complexes: Synthesis, characterization, and catalytic activity towards the reduction as well as condensation of nitriles
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The ligands 9,10-phenanthrenequinone-N4-substituted thiosemicarbazones (HL1-3) and their ruthenium(II) complexes were synthesized and characterized by elemental and spectroscopic methods. The ligands are tridentate, monobasic chelating ligands with O, N, and S as the donor sites and are in the thiol form in all the complexes. Catalytic studies showed that all the complexes displayed good catalytic activity towards the reduction of nitriles and also the condensation of nitriles with 2-aminoalcohol under solvent-free conditions.
- Anitha, Panneerselvam,Viswanathamurthi, Periasamy,Kesavan, Devarayan,Butcher, Ray Jay
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p. 321 - 334
(2015/10/20)
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- Ruthenium(II) 8-quinolinolates: Synthesis, characterization, crystal structure and catalysis in the synthesis of 2-oxazolines
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Abstract New octahedral ruthenium(II) complexes (1-4) have been synthesized from the reaction of ruthenium(II) precursors [RuHCl(CO)(EPh3)3] (E = P or As) with the bidentate Schiff base ligands, 2-((2,6-dimethylphenylimino)methyl)quinolin-8-ol (L1) and 2-((2,6-diisopropylphenylimino)methyl)quinolin-8-ol (L2) in ethanol. These complexes have been characterized by elemental analyses, IR, UV-Vis, 1H, 13C and 31P NMR and ESI-Mass spectroscopy. The molecular structure of the complex [RuCl(CO)(PPh3)2(L2)] (2) was determined by single-crystal X-ray diffraction, which reveals a distorted octahedral geometry around ruthenium(II) ion. The catalytic activity of the new complexes was evaluated for the condensation of nitriles with ethanolamine under solvent free conditions. The processes were operative with aromatic and heteroaromatic nitriles and tolerated several substitutional groups. The studies on the effect of substitution over ligands, coligands, reaction time, temperature and catalyst loading were carried out in order to find the best catalyst in this series of complexes and favorable reaction conditions. A probable mechanism for the catalytic condensation of nitrile has also been proposed. The catalyst was recovered and recycled up to five times without significant loss of its activity.
- Anitha,Manikandan,Prakash,Pachiyappan,Viswanathamurthi,Malecki
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p. 266 - 273
(2015/06/22)
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- Nickel-catalyzed ligand-free synthesis of benzoxazoles and oxazolines via isocyanide insertion
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A novel and efficient route to benzoxazoles and oxazolines involving a nickel-catalyzed three-component coupling reaction of iodobenzene, an amino alcohol and tert-butyl isocyanide has been developed. A wide array of products have been prepared in good to excellent yields in the absence of ligand.
- Wang, Jin-Mei,Jiang, Xiao,Tang, Ting,Zhu, Yong-Ming,Shen, Jing-Kang
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p. 1441 - 1453
(2014/07/07)
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- Hexaalkylguanidinium salts as ionic liquids - Applications in titanium and aluminium alcoholate assisted synthesis
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The solubility of titanium and aluminium alcoholates and of titanium tetrakis(trimethylsilanolate) in several hexaalkylguanidinium-based room temperature ionic liquids was screened. The solvent/solute combinations which displayed the highest alcoholate solubility and stability were applied as Lewis-acidic catalytic media for several dehydrating cyclocondensations: lactamisation of ω-aminocarboxylic acids, direct amidation of carboxylic acids, synthesis of oxazolines from carboxylic acids and 2-aminoethanol, lactonisation of 6-hydroxyhexanoic acid, and Paal-Knorr synthesis of pyrroles.
- Arkhipova, Maria,Eichel, Svetlana,Maas, Gerhard
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p. 56506 - 56517
(2015/02/05)
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- [3 + 2]-Cycloadditions of nitrile ylides after photoactivion of vinyl azides under flow conditions
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The photodenitrogenation of vinyl azides to 2H-azirines by using a photoflow reactor is reported and compared with thermal formation of 2H-azirines. Photochemically, the ring of the 2H-azirines was opened to yield the nitrile ylides, which underwent a [3 + 2]-cycloaddition with 1,3-dipolarophiles. When diisopropyl azodicarboxylate serves as the dipolarophile, 1,3,4-triazoles become directly accessible starting from the corresponding vinyl azide.
- Cludius-Brandt, Stephan,Kupracz, Lukas,Kirschning, Andreas
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supporting information
p. 1745 - 1750
(2013/10/22)
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- Polynuclear copper(ii) pyrazolate complexes: Temperature-dependent protonolysis reactions, crystal structures and high catalytic activity toward the condensation of nitriles with 2-aminoalcohol
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Reaction of Cu(OAc)2·H2O and 1H-pyrazole-3,5-dicarboxylic acid dimethyl ester (Hdcmpz) in MeOH at room temperature afforded one tetranuclear Cu(ii)/pyrazolate complex [{Cu 2(μ-OAc)2}2(μ-dcmpz)2/
- Wang, Ling,Guo, Bin,Li, Hong-Xi,Li, Qi,Li, Hai-Yan,Lang, Jian-Ping
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p. 15570 - 15580
(2013/11/06)
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- S-Co(II) cascade catalysis: Cyclocondensation of aromatic nitriles with alkamine
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A solvent-free S/Co(NO3)2 cascade catalyzed cyclocondensation reaction of aromatic nitriles with 3-amino-1-propanol or 2-aminoethanol has been successfully developed under thermal and microwave conditions. By this two-component protocol, mono- and bis-oxazines and oxazolines were selectively synthesized both in good to excellent yields and short reaction times. This catalytic system exhibits excellent chemoselectivity, and can be reused at least seven times without significant loss of activity in subsequent reactions.
- Ge, Haixia,Liu, Ping,Li, Xiangnan,Sun, Wei,Li, Jianli,Yang, Bingqin,Shi, Zhen
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p. 6591 - 6597
(2013/07/26)
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- DDQ-induced dehydrogenation of heterocycles for c-c double bond formation: Synthesis of 2-thiazoles and 2-oxazoles
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Strong as an Ox: 2-Thiazoles and 2-oxazoles are formed by oxidation of 2-thiazolines and 2-oxazolines without requiring substituents at the C4 and C5 positions. DDQ plays an important role as the oxidant in this transformation and metal is unnecessary. This general procedure shows good functional group tolerance and provides a wide variety of 2-thiazoles and 2-oxazoles in moderate to excellent yields.
- Li, Xiangnan,Li, Cheng,Yin, Bing,Li, Cong,Liu, Ping,Li, Jianli,Shi, Zhen
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supporting information
p. 1408 - 1411
(2013/07/26)
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- Traceless chelation-controlled rhodium-catalyzed intermolecular alkene and alkyne hydroacylation
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A new functional-group tolerant, rhodium-catalyzed, sulfide-reduction process is combined with rhodium-catalyzed chelation-controlled hydroacylation reactions to give a traceless hydroacylation protocol. Aryl- and alkenyl aldehydes can be combined with both alkenes, alkynes and allenes to give traceless products in high yields. A preliminary mechanistic proposal is also presented. Traceless catalysis: The powerful combination of a chelation-controlled hydroacylation process and a new rhodium-catalyzed sulfide reduction gave the products of traceless hydroacylation. Aryl- and alkenyl aldehydes can be combined with alkenes, alkynes, and allenes to deliver traceless products in high yields (see scheme). Copyright
- Hooper, Joel F.,Young, Rowan D.,Weller, Andrew S.,Willis, Michael C.
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supporting information
p. 3125 - 3130
(2013/03/28)
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- A mild and efficient synthesis of 2-oxazolines via transamidation- cyclodehydrosulfurisation of thioamides with 2-aminoethanol
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Transamidation of thioamides with 2-aminoethanol, followed by cyclodehydrosulfurisation of the resultant N-(β-hydroxyethyl)thioamides, has been utilised for the mild and efficient synthesis of 2-oxazolines. The developed protocol was found to be of general applicability. Georg Thieme Verlag KG Stuttgart · New York.
- Goud, D. Raghavender,Pathak, Uma
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p. 3678 - 3682
(2013/02/22)
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- A general and efficient palladium-catalyzed carbonylative synthesis of 2-aryloxazolines and 2-aryloxazines from aryl bromides
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Oxazoline is OK! A general and efficient method for the synthesis of oxazolines has been developed (see scheme). This allowed the preparation of 27 five-membered-ring heterocycles and 11 six-membered-ring heterocycles in moderate to good yields. Copyright
- Wu, Xiao-Feng,Neumann, Helfried,Neumann, Stephan,Beller, Matthias
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p. 13619 - 13623
(2013/01/15)
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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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- Solvent-free tandem synthesis of 2-thiazolines and 2-oxazolines catalyzed by a copper catalyst
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Tandem reactions of nitriles with 2-aminoethanethiol hydrochloride or amino alcohols in the presence of a catalytic amount of cupric methacrylate (Cu II2L4, L = methacrylate) were employed to prepare 2-thiazolines and 2-ox
- Li, Xiangnan,Zhou, Baoyue,Zhang, Jin,She, Mengyao,An, Shujuan,Ge, Haixia,Li, Cong,Yin, Bing,Li, Jianli,Shi, Zhen
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experimental part
p. 1626 - 1632
(2012/05/04)
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- A convenient synthesis of 2-oxazolines and 2-benoxazoles with PPh3-DDQ as the dehydrating reagent
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2-Oxazolines and 2-benoxazoles were synthesized in high yields from acylamino alcohols and acylaminophenols, respectively, with triphenylphosphine- 2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DDQ) as the dehydrating and activating reagent. The synthesis was accomplished under neutral conditions.
- Xu, Quancai,Li, Zhengning,Chen, Huiying
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experimental part
p. 925 - 932
(2012/01/03)
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- A powerful palladium-catalyzed multicomponent process for the preparation of oxazolines and benzoxazoles
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Efficient and convenient three-component couplings of an aryl halide, isocyanide, and an amino alcohol under palladium catalysis provide a range of oxazolines and benzoxazoles in excellent yield.
- Boissarie, Patrick J.,Hamilton, Zoe E.,Lang, Stuart,Murphy, John A.,Suckling, Colin J.
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supporting information; experimental part
p. 6256 - 6259
(2012/01/06)
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- Synthesis of 2-oxazolines via boron esters of N-(2-hydroxyethyl) amides
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A new, convenient, one-pot process is presented for the synthesis of 2-oxazolines in high yields (75-94%) via boron esters of N-(2-hydroxyethyl) amides. The procedure involves thermolysis of the boron esters at 240-260 °C, in the presence of solid CaO as an acid scavenger and allows the preparation of oxazolines from hydroxyethyl amides of aliphatic and aromatic monocarboxylic acids.
- Ilkgul, Baris,Gunes, Deniz,Sirkecioglu, Okan,Bicak, Niyazi
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experimental part
p. 5313 - 5315
(2010/11/03)
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- Poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′- tetrabromobenzene-1, 3-disulfonamide as new efficient reagents for conversion of alcohols to THP ethers and aldehydes to oxazoline compounds
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This paper is concerned with an easy preparation of THP ethers from primary, secondary and tertiary alcohols and oxazoline compounds from various aldehydes using poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA] as new and efficient reagents under ambient conditions without over-oxidation.
- Ghorbani-Vaghei,Akbari-Dadamahaleh,Amiri
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experimental part
p. 301 - 307
(2010/09/03)
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- A facile synthesis of 2-oxazolines using a PPh3-DDQ system
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A facile and efficient synthesis of 2-oxazolines from N-(2-hydroxyethyl)amides using a triphenylphosphine-2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DQQ) system is described. The reaction proceeds under neutral and mild conditions, and excellent yields are obtained.
- Xu, Quancai,Li, Zhengning
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experimental part
p. 6838 - 6840
(2010/04/29)
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- The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions
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β-Hydroxy amides 6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85-99%), as well as a tetrahydro-1,3-oxazepine (31%).
- Petersson, Maria J.,Jenkins, Ian D.,Loughlin, Wendy A.
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supporting information; experimental part
p. 739 - 746
(2009/06/20)
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- A divergent synthesis of minor groove binders with tail group variation
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A new synthesis of polyamide minor groove binders in which diversity is introduced by the nucleophilic substitution of a 2-sulfido-1,3,2- diazaphospholidinyloxy substituent by volatile secondary amine nucleophiles is described. Such a method has potential
- Breen, David,Kennedy, Alan R.,Suckling, Colin J.
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scheme or table
p. 178 - 186
(2009/04/07)
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- Preparation of an improved sulfonated carbon-based solid acid as a novel, efficient, and reusable catalyst for chemoselective synthesis of 2-oxazolines and bis-oxazolines
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A highly sulfonated carbon as an efficient, recyclable, nontoxic, and green solid acid catalyst was readily synthesized by simultaneous sulfonation, dehydration, and carbonization of sucrose in sulfuric acid and was characterized by FT-IR, TG-DTG, XRD, and CHNS analysis, neutralization potentiometric titration, and SEM techniques. This new catalyst was used for preparation of 2-oxazolines and bis-oxazolines by reaction of β-aminoethanol with nitriles under reflux conditions. Sonication of this system enhanced the catalytic activity of the carbon-based solid acid and led to higher product yields and shorter reaction times. Another advantage of the system under ultrasonic irradiation is the ability to carry out large-scale reactions. In two cases, the catalyst was reused several times without loss of its activity.
- Mirkhani, Valiollah,Moghadam, Majid,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Mahdavi, Mohammad
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experimental part
p. 1489 - 1494
(2010/07/04)
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- METHOD FOR PRODUCING 2-OXAZOLINE ANALOGUE OR 1,3-OXAZINE ANALOGUE
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The present invention is a method for producing a 2-oxazoline analogue or a 1,3-oxazine analogue represented by the following general formula (3) by reacting a 1,2-aminoalcohol compound or a 1,2-aminothiol compound with an α,α-dihaloamine compound. (In the formula, n represents 0 or 1, and R represents an oxygen atom or a sulfur atom. R1, R2 and R3 each represents an atom or a group shown in Group 1 to Group 3, and R° represents an atom or a group shown in Group 2 or Group 3. Two or more of R1, R2 and R3 may be bonded to each other to form a ring. Group 1: a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a carboxyl group, a sulfonyl group, a sulfinoyl group or a sulfenyl group; Group 2: an alkyl group, which may have an arbitrary substituent, an aryl group or an aralkyl group; and Group 3: an alkyl-substituted, aryl-substituted or aralkyl-substituted oxy group, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, a thio group, a sulfonyl group, a sulfinoyl group or a sulfenyl group)
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Page/Page column 14
(2008/12/07)
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- Convenient one-pot synthesis of 2-oxazolines from carboxylic acids
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Simple one-pot methods for preparation of 2-oxazolines have been developed using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). Treatment of a mixture of carboxylic acids and 2-haloethylammonium salts with DMT-MM in methanol
- Hioki, Kazuhito,Takechi, Yumiko,Kimura, Noriyo,Tanaka, Hiroyuki,Kunishima, Munetaka
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experimental part
p. 1735 - 1737
(2009/10/10)
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- Practical reduction of oxazolines to alcohols
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A two-step, one-pot procedure using methyl chloroformate and lithium borohydride was developed to transform 2-substituted-oxazolines into alcohols. This methodology is compatible with a wide range of substrates including heterocyclic, aromatic, and aliphatic functionalized 2-oxazolines. Best results are obtained with electron-rich and ortho substituted 2-aryl-oxazolines.
- Bernardi, Anna,Ouellet, Stéphane G.,Angelaud, Remy,O'Shea, Paul D.
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supporting information; experimental part
p. 6707 - 6708
(2009/04/07)
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- Efficient oxidative conversion of aldehydes to 2-substituted oxazolines and oxazines using (diacetoxyiodo)benzene
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An efficient synthesis of 2-substituted oxazolines from aldehydes and 2-amino alcohol using (diacetoxyiodo)benzene as an oxidant, is reported. (Diacetoxyiodo)benzene acts as a mild dehydrogenating agent to convert the initially formed oxazolidine from ald
- Karade, Nandkishor N.,Tiwari, Girdharilal B.,Gampawar, Sumit V.
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p. 1921 - 1924
(2008/03/27)
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- Synthesis of 2-oxazolines and 2-thiazolines using lanthanide amino alkoxide
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New 2-oxazolines and 2-thiazolines are prepared from phenacysulfonylacetic acid methyl ester using lanthanide amino alkoxide. Copyright Taylor & Francis Group, LLC.
- Padmavathi,Reddy, B. Chandra Obula,Thriveni,Mohan, A.V. Nagendra
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p. 3127 - 3142
(2008/02/13)
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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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