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Paper | Regular issue | Vol 43, No. 8, 1996, pp.1687-1697
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7502
Research on Antiviral Agents. 5. Lithiation of 6-Methyluracil as a New and Efficient Entry to C(6)-Substituted Uracils

Maurizio Botta,* Raffaele Saladino, Giuliano delle Monache, Gabriella Gentile, and Rosario Nicoletti*

*Dipartimento Agrochimico, Universita degli studi di Viterbo "La Tuscia", Via San Camillo de Lellis, 01100 Viterbo, Italy


Synthesis of numerous C(6)-substituted uracils can be effected by lithiation of N(1),N(3)-substituted 6-methyluracils (1) and (4) with LiHMDS, followed by the reaction of the resulting lithio derivatives with carbon, sulfur, and selenium electrophiles. The unexpected migration of the N(1)-benzoyl group in the metalation-alkylation and the high stereoselectivity obtained in the reaction with substituted cyclohexanones are also reported.