Cu-Catalyzed Cycloaromatization and Amination of 2-Bromoaryl Nitriles, Terminal Alkynes, and Amines for 1-Aminoisoquinoline Synthesis.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-19 DOI:10.1021/acs.orglett.5c01258

Zhennan Lei,Saihong Wan,Feng Liu,Jianyu Dong,Yongbo Zhou

引用次数: 0

Abstract

We report a copper-catalyzed 6-endo-dig cycloaromatization and amination of 2-bromoaryl nitriles, terminal alkynes, and amines for efficient and selective synthesis of 1-aminoisoquinolines, which involves difunctionalization of the cyano group with amination of its carbon atom. A variety of 1-aminoisoquinolines, as well as derivatives of modified amino-containing drug molecules, are readily achieved in water. Cu(III)-acetylide serves as intermediate and governs the exclusive 6-endo-dig selectivity, suppressing undesired 5-exo-dig byproducts.

查看原文本刊更多论文

铜催化2-溴芳基腈、末端炔和胺的环芳香化和胺化合成1-氨基异喹啉。

我们报道了铜催化的2-溴芳基腈、末端炔和胺的6-内环芳构化和胺化，以高效和选择性地合成1-氨基异喹啉，其中涉及氰基与碳原子的胺化的双官能化。各种1-氨基异喹啉，以及修饰的含氨基药物分子的衍生物，很容易在水中得到。Cu(III)-乙酰基酯作为中间体，控制6-内切选择性，抑制不需要的5-外切副产物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.