无过渡金属的 Minisci 反应：异喹啉、喹啉和喹喔啉的酰化反应。

A transition metal-free Minisci reaction: acylation of isoquinolines, quinolines, and quinoxaline.

机构信息

Department of Organic Chemistry, Indian Institute of Science , Bangalore 560 012, Karnataka, India.

出版信息

J Org Chem. 2014 May 2;79(9):3856-65. doi: 10.1021/jo500294z. Epub 2014 Apr 15.

Abstract

Transition metal-free acylation of isoquinoline, quinoline, and quinoxaline derivatives has been developed employing a cross dehydrogenative coupling (CDC) reaction with aldehydes using substoichiometric amount of TBAB (tetrabutylammonium bromide, 30 mol %) and K2S2O8 as an oxidant. This intermolecular acylation of electron-deficient heteroarenes provides an easy access and a novel acylation method of heterocyclic compounds. The application of this CDC strategy for acylation strategy has been illustrated in synthesizing isoquinoline-derived natural products.

摘要

发展了一种无过渡金属的酰化方法，可通过与醛的交叉脱氢偶联（CDC）反应，使用亚化学计量的四丁基溴化铵（TBAB，30 mol %）和过二硫酸钾（K2S2O8）作为氧化剂，对异喹啉、喹啉和喹喔啉衍生物进行酰化。这种缺电子杂芳烃的分子间酰化反应为杂环化合物提供了一种简便的酰化方法。该 CDC 策略在酰化策略中的应用已在合成异喹啉衍生的天然产物中得到了说明。