Heterocyclic synthesis with 4-benzoyl-1-cyanoacetylthiosemicarbazide: Selective synthesis of some thiazole, triazole, thiadiazine, pyrrylthiazole, and pyrazolo[1,5-a]triazine derivatives

被引：37

作者：

Bondock, Samir ^{[1
]}

Tarhoni, Abd El-Gaber ^{[1
]}

Fadda, Ahmed A. ^{[1
]}

机构：

[1] Mansoura Univ, Fac Sci, Dept Chem, Mansoura, Egypt

来源：

MONATSHEFTE FUR CHEMIE | 2008年 / 139卷 / 02期

关键词：

thiosemicarbazide; alpha-haloketones; thiazoline; triazole; thiadiazine;

D O I：

10.1007/s00706-007-0764-5

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

4-Benzoyl-1-cyanoacetylthiosemicarbazide undergoes coupling reaction with aromatic diazonium chloride to afford (arylhydrazono)thiosemicarbazide, which was reacted with phenacyl bromide regioselectivity to afford the thiazoline. The (arylhydrazono)thiosemicarbazide could be transformed into the pyrazolo[1,5-a]triazine. Heterocyclization of 4-benzoyl-1-cyanoacetylthiosemicarbazide with alpha-haloketones (bromoacetone and phenacyl bromide), ethyl iodide, and ethyl bromoacetate furnished the pyrrylthiazoles, 1,2,4- triazole, and 1,3,4-thiadiazine. The latter was coupled with aromatic diazonium chloride to give the bis(arylhydrazono)-thiadiazine. The mechanism for the formation of the title compounds was suggested and discussed.

引用

页码：153 / 159

页数：7

共 31 条

[1]

Utilization of α-halocarbonyl compounds in the synthesis of thiazole, thiadiazole, and thiophene derivatives [J].