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钯催化 N-酰基-o-炔基苯胺与异氰的环化反应:涉及 1,3-酰基迁移的快速构建官能化 2-氨基喹啉。

Palladium-Catalyzed Cyclization of N-Acyl- o-alkynylanilines with Isocyanides Involving a 1,3-Acyl Migration: Rapid Access to Functionalized 2-Aminoquinolines.

机构信息

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology , Guangzhou 510640 , China.

State Key Laboratory of Luminescent Materials and Devices , South China University of Technology , Guangzhou 510640 , China.

出版信息

Org Lett. 2018 Nov 16;20(22):7245-7248. doi: 10.1021/acs.orglett.8b03165. Epub 2018 Nov 5.

DOI:10.1021/acs.orglett.8b03165
PMID:30394094
Abstract

A simple and expedient approach for the synthesis of functionalized 2-aminoquinolines via palladium-catalyzed annulation of N-acyl- o-alkynylanilines with isocyanides has been developed with high atom economy, in which an unconventional 6- endo-dig cyclization process is observed. Further investigations of the mechanism demonstrated that an intramolecular acyl migration of the N-protecting groups was involved in this transformation.

摘要

发展了一种通过钯催化 N-酰基-邻炔基苯胺与异氰化物的环化反应来合成功能化 2-氨基喹啉的简便方法,具有高原子经济性,其中观察到一种非传统的 6-endo-dig 环化过程。对反应机理的进一步研究表明,N-保护基的分子内酰基迁移参与了这一转化。

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