Direct Synthesis of Disubstituted 3‐Isoquinolinone Derivatives through the Construction of C−N, C=O, and C(sp2)−C(sp3) Bonds under Transition‐Metal‐Free Conditions. Issue 3 (30th December 2022)

• Record Type: Journal Article
• Authors: Shi, Jianyi; Chen, Xia; Huang, Jingyun; Lu, Yantong; Yang, Zhendong; Zhong, Mingli; Zhu, Zhongzhi; Chen, Xiuwen
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 3(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-30
• Subjects: acetophenone -- dearomatization -- nitromethane -- trifunctionalization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201231
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The efficient three‐component cascade coupling reaction of 3‐haloisoquinolines, haloalkanes, and sp 3 ‐carbon nucleophiles (acetophenone or nitromethane) led to a series of structurally novel 1, 2‐disubstituted‐3‐isoquinolinones through the formation of C(sp 3 )−C(sp 2 ), C−N, and C=O bonds. The NaOAc‐promoted reaction described in this work is simple to operate, environment friendly, and highly selective. Abstract : A one‐step construction of C−N, C=O and C(sp 2 )−C(sp 3 ) bonds under transition‐metal‐free conditions for the synthesis of disubstituted 3‐isoquinolinone derivatives is reported. The reaction is characterized by wide substrate scope, high selectivity and environmental friendliness.