铜催化的 2H-苯并[b][1,4]噻嗪-3(4H)-酮和喹喔啉-2(1H)-酮的级联合成，分别从 AcSH 和 TsNH(2)中捕获 S 和 N 原子。

Copper-catalyzed cascade syntheses of 2H-benzo[b][1,4]thiazin-3(4H)-ones and quinoxalin-2(1H)-ones through capturing S and N atom respectively from AcSH and TsNH(2).

机构信息

Department of Chemistry, Zhejiang University, Xi Xi Campus, Hangzhou 310028, Zhejiang, People's Republic of China.

出版信息

J Org Chem. 2010 Aug 20;75(16):5768-71. doi: 10.1021/jo101253a.

PMID:20666413

Abstract

A copper-catalyzed cascade method has been developed to synthesize the 2H-benzo[b][1,4]thiazin-3(4H)-ones from 2-halo-N-(2-halophenyl)-acetamides 1 and AcSH via the S(N)2/deacetylation/coupling process, and to synthesize the quinoxalin-2(1H)-ones from 1 and TsNH(2) via the S(N)2/coupling/desulfonation process. The target products were obtained with diversity at three positions on their scaffolds.

摘要

一种铜催化的级联方法已经被开发出来，用于通过 S(N)2/去乙酰化/偶联过程，从 2-卤代-N-(2-卤代苯基)-乙酰胺 1 和 AcSH 合成 2H-苯并[b][1,4]噻嗪-3(4H)-酮，以及通过 S(N)2/偶联/脱硫过程，从 1 和 TsNH(2)合成喹喔啉-2(1H)-酮。目标产物在其支架的三个位置具有多样性。