Metal-Free Synthesis of 1,3,4-Oxadiazoles from N′-(Arylmethyl)hydrazides or 1-(Arylmethyl)-2-(arylmethylene)hydrazines

被引：16

作者：

Shang, Zhenhua ^{[1
,2
]}

Chu, Qianqian ^{[1
]}

Tan, Sheng ^{[3
]}

机构：

[1] Hebei Univ Sci & Technol, Hebei Res Ctr Pharmaceut & Chem Engn, Coll Chem & Pharmaceut Engn, Shijiazhuang 050018, Peoples R China

[2] Hebei Prov Key Lab Mol Chem Drugs, State Key Lab Breeding Base, Shijiazhuang 050018, Peoples R China

[3] Shijiazhuang Chem Engn Inst, Shijiazhuang 050000, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 07期

关键词：

oxadiazoles; cyclizations; oxidations; hydrazines; hydrazides; ONE-POT SYNTHESIS; ALDEHYDE N-ACYLHYDRAZONES; SOLID-PHASE SYNTHESIS; SUBSTITUTED 1,3,4-OXADIAZOLES; OXIDATIVE CYCLIZATION; CONVENIENT SYNTHESIS; FUNGICIDAL ACTIVITY; MOLECULAR-OXYGEN; CARBOXYLIC-ACIDS; DERIVATIVES;

D O I：

10.1055/s-0034-1379974

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and versatile metal-free synthesis of 1,3,4-oxadiazoles from N-(arylmethyl)hydrazides or 1-(arylmethyl)-2-(arylmethylene)hydrazines through oxidative dehydrogenation is reported. A range of 2,5-disubstituted 1,3,4-oxadiazoles were prepared by treating N-(arylmethyl)hydrazides with (diacetoxyiodo)benzene in acetonitrile or by treating 1-(arylmethyl)-2-(arylmethylene)hydrazines with [bis(trifluoroacetoxy)iodo]benzene in methyl tert-butyl ether. Aldehyde N-acylhydrazones and aldazines were initially generated in situ as intermediates.

引用

页码：1032 / 1040

页数：9

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