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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

Massari, Serena, Desantis, Jenny, Nannetti, Giulio, Sabatini, Stefano, Tortorella, Sara, Goracci, Laura, Cecchetti, Violetta, Loregian, Arianna and Tabarrini, Oriana 2017. 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. Organic and Biomolecular Chemistry 15 (37) , pp. 7944-7955. 10.1039/C7OB02085F

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Date of First Compliant Deposit: 24 September 2018
Date of Acceptance: 4 September 2017
Last Modified: 26 Sep 2018 05:19
URI: http://orca.cf.ac.uk/id/eprint/115211

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