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Pyrrolo[3,4-e][1,2,3]triazolo[1,5-a]pyrimidine and pyrrolo[3,4-d] [1,2,3]triazolo[1,5-a]pyrimidine. New tricyclic ring systems of biological interest

✍ Scribed by Antonino Lauria; Patrizia Diana; Paola Barraja; Anna Maria Almerico; Girolamo Cirrincione; Gaetano Dattolo

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
301 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Derivatives of the new ring system pyrrolo[3,4‐e][1,2,3] triazolo[1,5‐a]pyrimidine 6 were prepared in high yields in one step by reaction of 3‐azidopyrrole 3 and substituted acetonitriles. Compound 6b rearranged, upon heating in dimethyl sulfoxide in the presence of water, to pyrrolo[3,4‐d][1,2,3]triazolo‐[1,5‐a]pyrimidine 7.

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## Abstract The 7‐chloro‐3‐(2‐chlorobenzyl)‐ and 7‐chloro‐3‐(2‐fluorobenzyl)‐1,2,3‐triazolo[4,5‐__d__]pyrimidines (**1** and **4**), by nucleophilic replacement with some hydrazides, gave the corresponding 7‐hydrazidoderivatives (**2a‐e** and **5a‐e**). These, by heating in Dowtherm, underwent an i