钯催化酰肼的氧化O-H/N-H羰基化反应：合成取代的1,3,4-恶二唑-2(3H)-酮

Palladium-Catalyzed Oxidative O-H/N-H Carbonylation of Hydrazides: Access to Substituted 1,3,4-Oxadiazole-2(3H)-ones.

作者信息

Ji Fanghua, Li Xianwei, Guo Wei, Wu Wanqing, Jiang Huanfeng

机构信息

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.

出版信息

J Org Chem. 2015 Jun 5;80(11):5713-8. doi: 10.1021/acs.joc.5b00664. Epub 2015 May 20.

DOI:10.1021/acs.joc.5b00664

PMID:25973639

Abstract

A novel palladium-catalyzed oxidative annulation reaction for the C-O, C-N bond formations is developed. The intramolecular cyclocarbonylation provides an efficient and direct approach for the construction of valuable 1,3,4-oxadiazole-2(3H)-ones and their derivatives. The reaction also facilitated the convenient synthesis of BMS-191011, an opener of the cloned large-conductance Ca(2+)-activated potassium channel, providing an attractive method for medicinal chemistry.

摘要

开发了一种用于形成C-O、C-N键的新型钯催化氧化环化反应。分子内环羰基化反应为构建有价值的1,3,4-恶二唑-2(3H)-酮及其衍生物提供了一种有效且直接的方法。该反应还促进了克隆的大电导钙激活钾通道开放剂BMS-191011的便捷合成，为药物化学提供了一种有吸引力的方法。