Title : ( Facile synthesis of the new derivatives of 3-alkylsulfanyl-5-chloro-7-methyl- [1,2,4]triazolo[4,3-c]pyrimidine )
Authors: Mehdi Bakavoli , Mohammad Rahimizadeh , mahboobe siahkouhi nia , Ali Shiri ,
Abstract
Triazolopyrimidines are of interest not only for the synthesis of heterocyclic systems but also as compounds having biological activity and exhibiting, in particular, hypotensive, antiseptic, antiarrhythmic, and antiasthmatic properties[1,2]. Some methods for the preparation of these heterocyclic system are involves treatment of hydrazinopyrimidines with carbon disulfide or sodium nitrite in the presence of acetic acid [3] or condensation of the hydrazinopyrimidines with either formic acid or its orthoester [4] and also by the Dimroth rearrangement of imino derivatives of some pyrolopyridines in the presence of NaOH to obtain the hydrazinopyrimidine which were transformed into [1,2,4]triazolo[4,3- c]pyrimidines by treatment with acylhalides[5]. In this study, the reaction of 2-chloro-4-hydrazino-6-methylpyrimidine with carbonedisulfide in boiling pyridine led to the synthesis of 5-chloro-7-methyl- [1,2,4]triazolo[4,3-c]pyrimidine-3(2H)-thione. Subsequently, this precursor was alkylated by various alkyl halides in CH3CN and in the presence of triethylamine to give the corresponding 3-alkylsulfanyl-5-chloro-7-methyl- [1,2,4]triazolo[4,3-c]pyrimidine derivatives.
Keywords
, [1, 2, 4]triazolo[4, 3-c]pyrimidine-3(2H)-thione@inproceedings{paperid:1019373,
author = {Bakavoli, Mehdi and Rahimizadeh, Mohammad and Siahkouhi Nia, Mahboobe and Shiri, Ali},
title = {Facile synthesis of the new derivatives of 3-alkylsulfanyl-5-chloro-7-methyl- [1,2,4]triazolo[4,3-c]pyrimidine},
booktitle = {17th Iranian Seminar of Organic Chemistry},
year = {2010},
location = {بابلسر, IRAN},
keywords = {[1;2;4]triazolo[4;3-c]pyrimidine-3(2H)-thione},
}
%0 Conference Proceedings
%T Facile synthesis of the new derivatives of 3-alkylsulfanyl-5-chloro-7-methyl- [1,2,4]triazolo[4,3-c]pyrimidine
%A Bakavoli, Mehdi
%A Rahimizadeh, Mohammad
%A Siahkouhi Nia, Mahboobe
%A Shiri, Ali
%J 17th Iranian Seminar of Organic Chemistry
%D 2010