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以丙二腈为氰基源一锅法实现2,4-二芳基喹唑啉的区域选择性C-H活化碘化-氰化反应

One-pot regioselective C-H activation iodination-cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source.

作者信息

Yan Ziqiao, Ouyang Banlai, Mao Xunchun, Gao Wei, Deng Zhihong, Peng Yiyuan

机构信息

Key Laboratory of Functional Small Organic Molecule, Ministry of Education, Jiangxi Province's Key Laboratory of Green Chemistry, Jiangxi Normal University Nanchang Jiangxi 330022 China

Department of Chemistry, Nanchang Normal University Nanchang 330032 China.

出版信息

RSC Adv. 2019 Jun 11;9(32):18256-18264. doi: 10.1039/c9ra02979f. eCollection 2019 Jun 10.

Abstract

A one-pot cyanation of 2,4-arylquinazoline with NIS and malononitrile has been developed. The one-pot reaction includes two steps. The Rh-catalyzed selective C-H activation/iodization of 2,4-diarylquinazoline with NIS, and then Cu-catalyzed cyanation of the corresponding iodinated intermediate with malononitrile to selectively give 2-(2-cyanoaryl)-4-arylquinazolines or 2-(2,6-dicyanoaryl)-4-arylquinazolines in good to excellent yields.

摘要

已开发出一种用N - 碘代琥珀酰亚胺(NIS)和丙二腈对2,4 - 芳基喹唑啉进行一锅法氰化反应。该一锅法反应包括两个步骤。铑催化2,4 - 二芳基喹唑啉与NIS进行选择性C - H活化/碘化反应,然后铜催化相应的碘化中间体与丙二腈进行氰化反应,以良好至优异的产率选择性地得到2 - (2 - 氰基芳基)-4 - 芳基喹唑啉或2 - (2,6 - 二氰基芳基)-4 - 芳基喹唑啉。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1633/9064619/2c9e16ecc120/c9ra02979f-s1.jpg

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