Rearrangement of 3-(bromomethyl)quinoxalin-2(1H)-ones when exposed to 2-aminopyridines as a new method for the synthesis of 2-(imidazo[1,2-a]pyridin-2-yl)benzimidazoles

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-07-26 DOI:10.1007/s11172-024-4287-6

N. A. Zhukova, D. S. Perevalova, V. V. Syakaev, T. N. Beschastnova, A. T. Gubaidullin, O. G. Sinyashin, V. A. Mamedov

引用次数: 0

Abstract

A new efficient method was developed for the synthesis of 2-(imidazo[1,2-a]pyridin-2-yl)benzimidazoles based on the Mamedov rearrangement. The key step of the synthesis involves the acid-catalyzed rearrangement of spiroquinoxalinone derivatives as intramolecular cyclization products of 2-amino-1-[(quinoxalin-2(1H)-on-3-yl]methyl)pyridinium salts, which are generated by the modified Chichibabin reaction.

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3-(溴甲基)喹喔啉-2(1H)-酮与 2-氨基吡啶接触后的重排作为合成 2-(咪唑并[1,2-a]吡啶-2-基)苯并咪唑的新方法

基于马梅多夫重排法，开发了一种合成 2-(咪唑并[1,2-a]吡啶-2-基)苯并咪唑的高效新方法。合成的关键步骤是在酸催化下，将螺喹喔啉酮衍生物作为 2-氨基-1-[(喹喔啉-2(1H)-酮-3-基]甲基)吡啶鎓盐的分子内环化产物进行重排，而 2-氨基-1-[(喹喔啉-2(1H)-酮-3-基]甲基)吡啶鎓盐则是通过改良的 Chichibabin 反应生成的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.