specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides

The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH₂Cl, and MeSCH₂Cl in the K₂CO₃-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of...

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Veröffentlicht in:	Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2010-06, Vol.46 (2), p.200-205
Hauptverfasser:	Novakov, I. A, Orlinson, B. S, Nawrozkij, M. B, Mai, A, Artico, M, Rotili, D, Eremiychuk, A. S, Gordeeva, E. A, Brunilina, L. L, Este, J. A
Format:	Artikel
Sprache:	eng
Schlagworte:	5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones allyl chloro-methyl sulfide anti-HIV-1 agents Chemistry Chemistry and Materials Science Dimethylformamide methyl chloromethyl sulfide methyl iodide Organic Chemistry Pharmacy SN1- and SN2-substitution Sulfides
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Zusammenfassung:	The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH₂Cl, and MeSCH₂Cl in the K₂CO₃-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.
ISSN:	0009-3122 1573-8353
DOI:	10.1007/s10593-010-0492-3