Tandem C-C/C-N Bond Formation via Rh(III)-Catalyzed α-Fluoroalkenylation and Sequential Annulation of 2-Arylquinazolinones and gem-Difluorostyrenes

被引：8

作者：

Pang, Binghan ^{[1
]}

Wang, Yangyang ^{[1
]}

Hao, Liqiang ^{[1
]}

Wu, Gaorong ^{[1
]}

Ma, Zhihong ^{[2
]}

Ji, Yafei ^{[1
]}

机构：

[1] East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Minist Educ, Shanghai 200237, Peoples R China

[2] Biotalk Co LTD, Shanghai 200092, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期

基金：

中国国家自然科学基金;

关键词：

CRAFTS-TYPE CYCLIZATION; BIOLOGICAL EVALUATION; H FUNCTIONALIZATION; CATALYZED REACTION; QUINAZOLINE; AGENTS; ACIDS; RUTAECARPINE; ACETANILIDES; INHIBITORS;

D O I：

10.1021/acs.joc.2c02006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method of Rh(III)-catalyzed coupling reaction between 2-arylquinazolinones and gem-difluorostyrenes has been developed. In this work, two diverse structures of monofluoroalkenes and isoindolo[1,2-b]quinazolin-10(12H)-one derivatives were respectively synthesized by controlling the amount of additives (Ca(OH)2 and AgNTf2) to achieve controlled stepwise breaking of the C-F bonds of gem-difluorostyrenes. This reaction has the characteristics of a wide range of substrates and good functional group tolerance. Meanwhile, several control experiments were conducted and a plausible mechanism was proposed.

引用

页码：143 / 153

页数：11

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