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吲哚-C2位选择性碳-氧键形成反应合成与中环相连的多环吲哚酮或吲哚啉酮衍生物

Selective C-O Bond Forming Reactions at Indole-C2-Position toward Polycyclic Indolone or Indolinone Derivatives Tethered with Medium-Sized Rings.

作者信息

Wang Zongkang, Yin Liqiang, Wang Mengdan, Zhu Yilin, Yang Yajie, Cheng Lu, Wang Chengyu, Li Yanzhong

机构信息

School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai, 200241, China.

School of Chemistry and Chemical Engineering, Linyi University, Shuangling Road, Linyi, Shandong 276000, China.

出版信息

Org Lett. 2022 Sep 2;24(34):6272-6276. doi: 10.1021/acs.orglett.2c02398. Epub 2022 Aug 18.

DOI:10.1021/acs.orglett.2c02398
PMID:35980745
Abstract

A methodology involving the chemoselective synthesis of tetracyclic [1,3]oxazino[3,2-]indol-4-one or tetracyclic [1,3]oxazino[3,2-]indoline-4-one tethered with a medium-sized ring by cross dehydrogenative coupling (CDC) or nucleophilic addition (NA) reaction has been developed. [1,3]Oxazino[3,2-]indol-4-one compounds fused with a medium-sized ring were constructed through a CDC reaction in the presence of I and KCO. Whereas, [1,3]oxazino[3,2-]indoline-4-ones tethered with a medium-sized ring were obtained with a TfOH system by NA reaction.

摘要

已开发出一种方法,该方法涉及通过交叉脱氢偶联(CDC)或亲核加成(NA)反应进行化学选择性合成与中型环相连的四环[1,3]恶嗪并[3,2 -]吲哚 - 4 - 酮或四环[1,3]恶嗪并[3,2 -]二氢吲哚 - 4 - 酮。与中型环稠合的[1,3]恶嗪并[3,2 -]吲哚 - 4 - 酮化合物是在I和KCO存在下通过CDC反应构建的。而与中型环相连的[1,3]恶嗪并[3,2 -]二氢吲哚 - 4 - 酮是通过NA反应在TfOH体系中获得的。

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