High-yield regioselective thiation of biologically important pyrimidinones, dihydropyrimidinones and their ribo, 2’-deoxyribo and 2‘, 3’-dideoxyribo nucleosides.

Krzysztof Felczak, Maria Bretner, Tadeusz Kulikowskit, David Shugar

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

Convenient and high-yield regioselective thiation procedures based on the use of the Lawesson reagent in different solvents, are described for conversion of the 2- and 4-keto, and 2, 4-diketo pyrimidines to the corresponding 2(4)-thio, and 2, 4-dithio, derivatives. This method is applicable to thiation of the 4-keto groups of 5, 6-dihydropyrimidinones and pyrimidine nucleosides. The mild reaction conditions employed are such that it is the method of choice for compounds with labile glycosidic bonds, such as 5, 6-dihydropyrimidine nucleosides and the 2‘, 3’-dideoxynucleosides currently of interest as antiretroviral, including anti-HIV, agents.

Original languageEnglish (US)
Pages (from-to)245-261
Number of pages17
JournalNucleosides and Nucleotides
Volume12
Issue number2
DOIs
StatePublished - Feb 1 1993
Externally publishedYes

Bibliographical note

Funding Information:
This study was supported in part by a grant from the Polish State Committee for Scientific Research (KBN, No. 6 6253 92 03~101).

Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.

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