Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones

被引：107

作者：

Gao, Qinghe ^{[1
]}

Liu, Shan ^{[1
]}

Wu, Xia ^{[1
]}

Zhang, Jingjing ^{[1
]}

Wu, Anxin ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 12期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; C-C; INTRAMOLECULAR CYCLIZATION; AEROBIC OXIDATION; ARYL BROMIDES; CARBON; ACTIVATION; FUNCTIONALIZATION; CARBOACYLATION; OXYGENATION;

D O I：

10.1021/acs.orglett.5b01241

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for the synthesis of 1,3,4-oxadiazoles was established through direct annulation of hydrazides with methyl ketones. It was found that the use of K2CO3 as a base achieves an unexpected and highly efficient C-C bond cleavage. This reaction is proposed to go through oxidative cleavage of C-sp(3)-H bonds, followed by cyclization and deacylation.

引用

页码：2960 / 2963

页数：4

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