Microwave-assisted regioselective synthesis of acyclic nucleosides through an alkylating reaction with 2-oxa-1,4-butanediol diacetate
- 1 May 2006
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 84 (5) , 819-824
- https://doi.org/10.1139/v06-061
Abstract
An efficient and green procedure for the synthesis of purine acyclic nucleosides through microwave-assisted alkylation of various purine nucleobases with 2-oxa-1,4-butanediol diacetate in the absence of solvent and catalyst is described. The advantages of using this method include its environmental friendliness, simple manipulation, short reaction time, high regioselectivity, and good yields.Key words: acyclic nucleosides, microwave irradiation, regioselectivity, alkylation, 2-oxa-1,4-butanediol diacetate.Keywords
This publication has 13 references indexed in Scilit:
- Alkylation of 3,4-Dibromo-4-methyltetrahydropyran with Diethyl Malonate as a Key to Understanding the Electronic Nature of Chemo- and Regioselectivity of MoleculesRussian Journal of Organic Chemistry, 2005
- Microwave-Assisted Ring Opening of Epoxides with Pyrimidine Nucleobases: A Rapid Entry into C -Nucleoside SynthesisSynthesis, 2004
- Synthesis of Polyfunctional Aromatic Ring Systems (Phloroglucide Analogs) under Microwave IrradiationHelvetica Chimica Acta, 2003
- Natural phosphate as Lewis acid catalyst: a simple and convenient method for acyclonucleoside synthesisTetrahedron Letters, 2001
- 9-Vinylguanine: an easy access to aza-analogs of 2′,3′-dideoxyguanosineTetrahedron, 2001
- A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-DiacetylguanineThe Journal of Organic Chemistry, 1999
- A convenient synthesis of 9-(2-hydroxyethoxymethyl)guanine(acyclovir) and related compounds.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
- Nucleic acid related compounds. 47. Synthesis and biological activities of pyrimidine and purine "acyclic" nucleoside analogsJournal of Medicinal Chemistry, 1984
- Iodomethylethers from 1,3-dioxolane and 1,3-oxathiolane: preparation of acyclic nucleoside analogsTetrahedron Letters, 1979
- Novel substrate of adenosine deaminaseJournal of Medicinal Chemistry, 1971