Synthesis of ( Z) and ( E) α-alkenyl phosphonic acid derivatives of purines and pyrimidines

( Z) and ( E)-2-(purin-9-yl/ pyrimidin-1-yl)ethylen-1-ylphosphonic acid 10–18 were synthetized by Michael addition of heterocyclic base with the diethylethynylphosphonate and deprotection of the acyclic nucleoside phosphonate with bromotrimethylsilane. A simple synthesis of alkenyl phosphonic acids...

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Published inTetrahedron Vol. 54; no. 15; pp. 3807 - 3816
Main Authors Lazrek, H.B., Rochdi, A., Khaider, H., Barascut, J.-L., Imbach, J.-L., Balzarini, J., Witvrouw, M., Pannecouque, C., De Clercq, E.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.04.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NUCLEOTIDE ANALOGS
ACYCLOVIR
9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE
POTENTIAL ANTIVIRAL AGENTS
HIV
PHASE-TRANSFER CATALYSIS
ACYCLIC NUCLEOSIDE PHOSPHONATES
MICHAEL ADDITION
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Summary:( Z) and ( E)-2-(purin-9-yl/ pyrimidin-1-yl)ethylen-1-ylphosphonic acid 10–18 were synthetized by Michael addition of heterocyclic base with the diethylethynylphosphonate and deprotection of the acyclic nucleoside phosphonate with bromotrimethylsilane. A simple synthesis of alkenyl phosphonic acids of purines and pyrimidines using Michael addition is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00107-0