Zinc oxide-tetrabutylammonium bromide tandem as a highly efficient, green, and reusable catalyst for the Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters under solvent-free conditions-Reference-Cited by-同舟云学术

Zinc oxide-tetrabutylammonium bromide tandem as a highly efficient, green, and reusable catalyst for the Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters under solvent-free conditions

Published:2008-04-01 Issue:4 Volume:86 Page:317-324
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Zare Abdolkarim,Hasaninejad Alireza,Beyzavi Mohammad Hassan,Parhami Abolfath,Zare Ahmad Reza Moosavi,Khalafi-Nezhad Ali,Sharghi Hashem

Abstract

An efficient procedure for the synthesis of carboacyclic nucleosides via microwave-assisted Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters in the presence of catalytic amounts of zinc oxide (ZnO) and tetrabutylammonium bromide (TBAB) is described. The reactions proceed rapidly in good to excellent yields.Key words: ZnO–TBAB, green chemistry, Michael addition, nucleobase, solvent-free, microwave.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v08-022

Reference11 articles.

1. Microwave-assisted regioselective synthesis of acyclic nucleosides through an alkylating reaction with 2-oxa-1,4-butanediol diacetate

2. An efficient Mitsunobu coupling to adenine-derived carbocyclic nucleosides

3. A novel synthesis of 4′-thionucleosides and a potential stereospecific route to pyrimidine nucleosides

4. A fast and highly efficient protocol for Michael addition of N-heterocycles to α,β-unsaturated compound using basic ionic liquid [bmIm]OH as catalyst and green solvent

5. The efficient and chemoselective MoO3-catalyzed oxidation of sulfides to sulfoxides and sulfones with H2O2

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