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Molecular Iodine‐Promoted Transimination for the Synthesis of 6‐Phenylpyrido[2′,1′:2,3]imidazo[4,5‐c]quinoline and 6‐(Pyridin‐2‐yl)pyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2017-10-25 , DOI: 10.1002/ajoc.201700357
Satish Sunkari 1 , Siddiq Pasha Shaik 1 , Namballa Hari Krishna 1, 2 , Ayanampudi Venkata Subba Rao 1, 3 , Bheeshma Geetanjali Kodiripaka 1 , Abdullah Alarifi 4 , Ahmed Kamal 1, 2, 4
Affiliation  

An unprecedented, efficient I2‐mediated approach for the synthesis of 6‐phenylpyrido[2′,1′:2,3]imidazo[4,5‐c]quinoline heterocyclic skeletons has been achieved from the reaction of benzylamines and 2‐(imidazo[1,2‐a]pyridin‐2‐yl)anilines. This one‐pot protocol proceeds through an oxidation/transimination/cyclization/aromatization reaction sequence under metal‐free conditions to result in the formation of N−C and C−C bonds. A variety of benzylamines, including pyridin‐2‐ylmethanamine, were successfully employed under the optimized conditions as imine precursors in this irreversible transimination reaction with 2‐(imidazo[1,2‐a]pyridin‐2‐yl)anilines to give the corresponding imines. The subsequent cyclization step successfully generated the the corresponding 6‐phenylpyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines.

中文翻译:

分子碘促进的氨基转移反应合成6-苯基吡啶并[2',1':2,3]咪唑并[4,5-c]喹啉和6-(吡啶-2-基)吡啶[2',1': 2,3]咪唑并[4,5-c]喹啉

苄胺与2-(-)的反应实现了前所未有的,高效的I 2介导的合成6-苯基吡啶并[2',1':2,3]咪唑并[4,5 -c ]喹啉杂环骨架的方法。咪唑并[1,2 - a ]吡啶-2-基)苯胺。该一锅法实验流程是在无金属的条件下进行氧化/氨基转移/环化/芳构化反应过程,从而导致NC和CC键的形成。在优化条件下,成功地使用了各种吡啶胺(包括吡啶-2-基甲胺)作为亚胺前体,与2-(咪唑并[1,2- a]] pyridin-2-yl)苯胺得到相应的亚胺。随后的环化步骤成功生成了相应的6-苯基吡啶并[2',1':2,3]咪唑并[4,5 -c ]喹啉。
更新日期:2017-10-25
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