使用 DMF 作为双合成子，铜催化β-(2-氨基苯基)-α,β-炔酮合成氨基喹啉。

Copper-catalyzed synthesis of aminoquinolines from β-(2-aminophenyl)-α,β-ynones using DMF as dual synthon.

机构信息

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, Republic of China.

Department of Chemistry, Faculty of Engineering and Technology, SRM Institute of Science and Technology, Kattankulathur, Chennai-603203, India.

出版信息

Chem Commun (Camb). 2020 Jun 16;56(48):6488-6491. doi: 10.1039/d0cc03033c.

DOI:10.1039/d0cc03033c

PMID:32458882

Abstract

A new and efficient method has been developed for the synthesis of 4-aminoquinoline through aerobic Cu(i)-catalyzed cyclization of β-(2-aminophenyl)-α,β-ynones. Under the optimized conditions, DMF could serve as a methine source to introduce C2 carbon and a nitrogen source to incorporate amino functionality in the 4th position. Mechanistic studies using 13C- and DMF-d7 revealed that the methine group was derived from a methyl substituent.

摘要

一种新的、有效的方法已经被开发出来，用于通过有氧 Cu(i)-催化的β-(2-氨基苯基)-α,β-炔酮的环化反应来合成 4-氨基喹啉。在优化的条件下，DMF 可以作为一个亚甲基源来引入 C2 碳，并且作为一个氮源来在 4 位引入氨基官能团。使用 13C-和 DMF-d7 的机理研究表明，亚甲基基团来源于一个甲基取代基。