Abstract
Cyclocondensations of diethyl benzylidenemalonate with 3-amino-5-methylpyrazole, 3,5-diamino-1,2,4-triazole, 3,4,5-triamino-1,2,4-triazole, and 2-amino-benzimidazole in alcohols take a single route and lead to the formation of functionally substituted partially hydrogenated pyrazolo-, triazolo[1,5-a]-pyrimidin-5-ones and pyrimido[1,2-a]benzimidazol-2-one respectively. From reaction mixtures involving 3-amino-1,2,4-triazole and its 5-methylsulfanyl analog in methanol the intermediate products of heterocyclization were isolated forming as a result of alkylation with the β-carbon of the unsaturated ester the endocyclic nucleophilic sites of aminoazoles. The structure of one among the products obtained, diethyl(3-amino-5-methylsulfanyl-1,2,4-triazol-2-yl)benzylmalonate was proved by X-ray crystallography. In DMF the same reagents yielded mixtures of partially hydrogenated triazolo[1,5-a]pyrimidin-5-ones.
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Original Russian Text © V.V. Lipson, T.M. Karnozhitskaya, S.M. Desenko, S.V. Shishkina, O.E. Shishkin, V.I. Musatov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 2, pp. 257–263.
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Lipson, V.V., Karnozhitskaya, T.M., Desenko, S.M. et al. Reactions of α-aminoazoles with diethyl benzylidenemalonate. Russ J Org Chem 43, 249–255 (2007). https://doi.org/10.1134/S1070428007020169
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DOI: https://doi.org/10.1134/S1070428007020169