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Efficient and regioselective one-step synthesis of 7-aryl-5-methyl- and 5-aryl-7-methyl-2-amino-[1,2,4]triazolo[1,5-a]pyrimidine derivatives.

Efficient and regioselective one-step synthesis of 7-aryl-5-methyl- and 5-aryl-7-methyl-2-amino-[1,2,4]triazolo[1,5-a]pyrimidine derivatives.
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Massari S, Desantis J, Nannetti G, Sabatini S, Tortorella S, Goracci L, Cecchetti V, Loregian A, Tabarrini O,


Massari S, Desantis J, Nannetti G, Sabatini S, Tortorella S, Goracci L, Cecchetti V, Loregian A, Tabarrini O, (click to view)

Massari S, Desantis J, Nannetti G, Sabatini S, Tortorella S, Goracci L, Cecchetti V, Loregian A, Tabarrini O,

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Organic & biomolecular chemistry 2017 09 13() doi 10.1039/c7ob02085f
Abstract

Two facile and efficient one-step procedures for the regioselective synthesis of 7-aryl-5-methyl- and 5-aryl-7-methyl-2-amino-[1,2,4]triazolo[1,5-a]pyrimidines have been developed, via reactions of 3,5-diamino-1,2,4-triazole with variously substituted 1-aryl-1,3-butanediones and 1-aryl-2-buten-1-ones, respectively. The excellent yield and/or regioselectivity shown by the reactions decreased when ethyl 5-amino-1,2,4-triazole-3-carboxylate was used. [1,2,4]Triazolo[1,5-a]pyrimidine being a privileged scaffold, the procedures herein reported may be useful for the preparation of biologically active compounds. In this study, the preparation of a set of compounds based on the [1,2,4]triazolo[1,5-a]pyrimidine scaffold led to the identification of compound 20 endowed with a very promising ability to inhibit influenza virus RNA polymerase PA-PB1 subunit heterodimerization.

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