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Paper | Regular issue | Vol 94, No. 5, 2017, pp. 912 - 922
Published online: 27th April, 2017
DOI: 10.3987/COM-17-13696
Selective N1-Alkylation of 1,3-Dibenzoyluracils: One-Pot Way to N1-Monosubstituted Uracil Derivatives

Alexander Ozerov,* Mikhail Novikov, Anastasiya Khandazhinskaya, and Pavel Solyev

*Department of Pharmaceutical & Toxicological Chemistry, Volgograd State Medical University, Pavshikh Bortsov Sq. 1, Volgograd, 400131, Russia

Abstract

A new method for synthesis of N1-monosubstituted uracils and 5- and 6-methyluracil derivatives was developed. It consists in the selective N1-deprotection of N1,N3-dibenzoyluracils in anhydrous dimethylformamide in the presence of potassium carbonate at room temperature and subsequent N1-alkylation by allyl, benzyl or phenacyl type halides or by primary alcohols toluenesulfonates conducted one-pot without isolation of the intermediates. Final N3-debenzoylation by aqueous-alcoholic solution of ammonia affords the corresponding N1-monosubstituted uracil derivatives with overall yields of 52-84%.

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