- Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles
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We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazoles using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher atom, step, and redox economies and exc
- An, Jie,Lai, Zemin,Li, Hengzhao,Peng, Mengqi,Sun, Yanhao,Yan, Zihan,Yang, Ruoyan,Zhang, Yuntong
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p. 748 - 753
(2022/02/02)
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- Synthesis method of benzimidazole compound based on iron catalytic oxidation-reduction coupling reaction
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The invention belongs to the field of organic synthesis, and relates to a benzimidazole compound synthesis method based on an iron catalytic oxidation-reduction coupling reaction. According to the method, o-nitroaniline compounds and alcohol compounds are used as raw materials, and the benzimidazole compounds are generated through iron-catalyzed redox coupling reaction in the presence of an iron catalyst and a proton donor. The method provided by the invention provides a new way for the synthesis of benzimidazole drugs and pesticides. Compared with a traditional benzimidazole compound synthesis method with o-phenylenediamine compounds and carboxylic acid or carboxylic acid derivatives as raw materials, the method has the advantages that the atom utilization rate of the whole process is increased, the production cost is reduced, and waste gas, waste liquid and waste solid generated in the production process is reduced.
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- Rhodium(III)-Catalyzed Directed C?H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles
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An efficient rhodium-catalyzed direct C?H amidation of N-nitrosoanilines with 1,4,2-dioxazol-5-ones as amidating agents has been developed. This method featured mild reaction conditions, a wide substrate scope and satisfactory yields. Besides, the amidated products could be readily converted to pharmaceutically valuable 1,2-disubstituted benzimidazoles via an HCl-mediated deprotection/cyclization process in one pot.
- Chen, Yanyu,Zhang, Rong,Peng, Qiujun,Xu, Lanting,Pan, XianHua
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supporting information
p. 2804 - 2808
(2017/10/20)
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- Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement
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A Beckmann-type rearrangement of o-hydroxy and o-aminoaryl N-H ketimines has been developed to prepare benzoxazoles and N-Ts benzimidazoles, respectively. The ketimine derivatives were easily prepared by condensation of ammonia with the corresponding ketones and (diacetoxyiodo)benzene was found to act as an efficient oxidant to trigger the [1,2]-aryl migration towards the formation of the desired heterocycles. Depending on the substitution pattern, the results revealed another mechanistic pathway through which benzisoxazoles or 1H-indazoles could be formed. The Beckmann-type rearrangement strategy was applied to the synthesis of benzimidazole-containing biorelevant targets such as chlormidazole and clemizole.
- Zhang, Xiaohui,Huang, Ruofeng,Marrot, Jér?me,Coeffard, Vincent,Xiong, Yan
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p. 700 - 708
(2015/02/02)
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- Benzimidazoles as new potent and selective DP antagonists for the treatment of allergic rhinitis
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A series of 2-substituted N-benzyl benzimidazole containing molecules has been synthesized and its structure-activity relationship for the human DP receptor has been evaluated. Selective DP antagonists with nanomolar potency for the DP receptor were identified in this novel series of benzimidazoles.
- Beaulieu, Christian,Wang, Zhaoyin,Denis, Danielle,Greig, Gillian,Lamontagne, Sonia,O'Neill, Gary,Slipetz, Deborah,Wang, Jennifer
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p. 3195 - 3199
(2007/10/03)
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