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Synthesis 2019; 51(11): 2311-2317
DOI: 10.1055/s-0037-1611765
DOI: 10.1055/s-0037-1611765
paper
Regioselective Synthesis of 5-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines from β-Enamino Diketones
The authors are grateful for financial support from the Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS/CNPq – PRONEX – Grant No. 16/2551-0000477-3) and Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, Grant No. 407898/2018-2), and for fellowships from CNPq (V.P.A.) and CAPES (M.M.).Further Information
Publication History
Received: 30 January 2019
Accepted after revision: 01 March 2019
Publication Date:
21 March 2019 (online)
![](https://www.thieme-connect.de/media/synthesis/201911/lookinside/thumbnails/ss-2019-m0062-op_10-1055_s-0037-1611765-1.jpg)
Abstract
The use of β-enamino diketones as an easy entry to the regioselective synthesis of [1,2,4]triazolo[1,5-a]pyrimidines is reported. These ketones reacted with 3-amino-1H-1,2,4-triazoles to furnish exclusively 6-substituted 5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines in yields of up to 95%. The regioselectivity of the reactions performed was maintained regardless of the substituent in the starting ketone or aminoazole.
Key words
β-enamino diketones - 1,3-diones - triazolopyrimidines - aminotriazoles - fluorinated heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611765.
- Supporting Information
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