Preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles via chemoselective cyclocondensation of electrophilically activated nitroalkanes to (thio)semicarbazides or thiohydrazides

被引：12

作者：

Aksenov, Nicolai A. ^{[1
]}

Arutiunov, Nikolai A. ^{[1
]}

Kirillov, Nikita K. ^{[1
]}

Aksenov, Dmitrii A. ^{[1
]}

Aksenov, Alexander V. ^{[1
]}

Rubin, Michael ^{[1
,2
]}

机构：

[1] North Caucasus Fed Univ, Dept Chem, 1a Pushkin St, Stavropol 355017, Russia

[2] Univ Kansas, Dept Chem, 1567 Irving Hill Rd, Lawrence, KS 66045 USA

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2020年 / 56卷 / 08期

基金：

俄罗斯基础研究基金会;

关键词：

nitroalkanes; 1,3,4-oxadiazoles; semicarbazides; 1,3,4-thiadiazoles; thiosemicarbazides; Bronsted acid catalysis; cascade reaction; nucleophilic cycloadition; ONE-POT SYNTHESIS; IN-VITRO; EFFICIENT SYNTHESIS; ANTI-HIV; DERIVATIVES; ACETAZOLAMIDE; ACID; SULFAMETHIZOLE; THIADIAZOLES; BENZOXAZOLES;

D O I：

10.1007/s10593-020-02775-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unusual reaction proceedingviathe electrophilic activation of nitroalkanes in the presence of polyphosphoric acid has been discovered. Subsequent nucleophilic attack with semicarbazides or thiosemicarbazides allows to access 2-amino-1,3,4-oxadiazoles and 2-amino-1,3,4-thiadiazoles, respectively.

引用

页码：1067 / 1072

页数：6

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