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Azines and Azoles: CXXII. New Regioselective Synthesis of 1-Substituted 6-Alkyluracils

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Abstract

Readily available 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones with primary alkyl- and arylamines in mild conditions (boiling in propan-2-ol) to give Schiff bases. In more rigid conditions (boiling in DMF), the reaction is accompanied by COS liberation and provides 1-substituted 6-alkyluracils. This previously unknown reaction possesses a considerable synthetic potential and can be considered as a new, general, and regioselective synthetic approach to 1-substituted 6-alkyluracils.

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Authors and Affiliations

  1. St. Petersburg State Chemical Pharmaceutical Academy, St. Petersburg, Russia

    V. N. Yuskovets, A. V. Moskvin, L. E. Mikhailov & B. A. Ivin

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  1. V. N. Yuskovets
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  2. A. V. Moskvin
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  3. L. E. Mikhailov
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  4. B. A. Ivin
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__________

Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 1, 2005, pp. 146–158.

Original Russian Text Copyright © 2005 by Yuskovets, Moskvin, Mikhailov, Ivin.

For communication CXXI, see [1].

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Yuskovets, V.N., Moskvin, A.V., Mikhailov, L.E. et al. Azines and Azoles: CXXII. New Regioselective Synthesis of 1-Substituted 6-Alkyluracils. Russ J Gen Chem 75, 134–146 (2005). https://doi.org/10.1007/s11176-005-0185-2

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  • DOI: https://doi.org/10.1007/s11176-005-0185-2

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