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Azines and azoles: CXXV. New regioselective synthesis of 1-amino-6-methyluracils

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Abstract

Readily accessible 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione reacts with substituted hydrazines and carboxylic acid hydrazides under mild conditions to give the corresponding hydrazones. Under severe conditions (heating in boiling dimethylformamide) the reaction is accompanied by extrusion of COS with formation of substituted 1-amino-6-methyluracils. Reactions of 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione with monosubstituted alkyl-and arylhydrazines take different pathways, depending on the conditions. Heating of equimolar mixtures of the reactants in ethanol or propan-1-ol leads to the formation of 2-substituted 5-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxamides rather than 1-amino-6-methyluracil derivatives.

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Authors and Affiliations

  1. St. Petersburg State Chemical and Pharmaceutical Academy, ul. Prof. Popova 14, St. Petersburg, 197376, Russia

    V. N. Yuskovets, B. A. Ivin & E. N. Kirillova

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  1. V. N. Yuskovets
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  2. B. A. Ivin
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  3. E. N. Kirillova
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Correspondence to V. N. Yuskovets.

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Original Russian Text © V.N. Yuskovets, B.A. Ivin, E.N. Kirillova, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 12, pp. 2007–2017.

For communication CXXIV see [1].

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Yuskovets, V.N., Ivin, B.A. & Kirillova, E.N. Azines and azoles: CXXV. New regioselective synthesis of 1-amino-6-methyluracils. Russ J Gen Chem 77, 2150–2161 (2007). https://doi.org/10.1134/S1070363207120134

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  • DOI: https://doi.org/10.1134/S1070363207120134

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