四氯化碳促进（2-炔基）芳基缩胺的环化反应合成多氯氮杂环。

Carbon Tetrachloride-Mediated Cyclization of (2-Alkynyl)arylaldimines for the Synthesis of Polychlorinated Nitrogen Heterocycles.

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale, Center for Excellence in Molecular Synthesis, and Department of Chemistry , University of Science and Technology of China , Hefei , Anhui 230026 , China.

Key Laboratory of Synthetic Chemistry of Natural Substances , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032 , China.

出版信息

Org Lett. 2019 Jul 19;21(14):5675-5678. doi: 10.1021/acs.orglett.9b02010. Epub 2019 Jul 10.

DOI:10.1021/acs.orglett.9b02010

PMID:31290329

Abstract

An unprecedented use of carbon tetrachloride to mediate the 6-endo-dig cyclization of (2-alkynyl)arylaldimines, generated in situ from (2-alkynyl)arylaldehydes and primary amines, has been developed via formal insertion of C═N and C≡C bonds into a C-Cl bond under catalyst-free conditions, providing convenient access to a range of structurally diverse polychlorinated 1,2-dihydroisoquinolines and heteroarene-fused nitrogen heterocycles.

摘要

一种前所未有的方法，即通过在无催化剂条件下，使 C═N 和 C≡C 键正式插入 C-Cl 键，将（2-炔基）芳基醛和伯胺原位生成的（2-炔基）芳基亚胺进行 6-endo-内型环化，从而实现了四氯化碳的空前应用，该方法为合成结构多样的多氯 1,2-二氢异喹啉和杂芳基稠合氮杂环提供了便捷途径。