Communications

An alternative synthesis of 7-amino-6-nitro-substituted azolo[1,5-a]pyrimidines

I. I. Butorin^a, O. A. Konovalova^a, P. A. Slepukhin^b, S. K. Kotovskaya^a, V. L. Rusinov<sup>a

a</sup> Institute of Chemical Engineering, Ural Federal University, Ekaterinburg, Russian Federation
^b I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation

Abstract: New 7-amino-6-nitro-substituted [1,2,4]triazolo- and pyrazolo[1,5-a]pyrimidines were synthesized by an alternative strategy based on amino azoles and 2-nitro-3-(p-tolylamino)acrylonitrile. Unexpectedly, 3,5-dinitro-N-(p-tolyl)pyridine-2,6-diamine was formed when the starting 5-amino-1,2,4-triazoles contained NO₂ or CF₃ substituents.

Keywords: [1,2,4]triazolo[1,5-a]pyrimidines, pyrazolo[1,5-a]pyrimidines, nitro synthons, dinitropyridines, acrylonitrile, DFT.

Language: English

DOI: 10.1016/j.mencom.2024.09.026

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