Next Article in Journal
Development of Designed Site-Directed Pseudopeptide-Peptido-Mimetic Immunogens as Novel Minimal Subunit-Vaccine Candidates for Malaria
Previous Article in Journal
Microwave Assisted Synthesis of Some New Heterocyclic Spiro-Derivatives with Potential Antimicrobial and Antioxidant Activity
Article Menu

Article Versions

Export Article

Open AccessArticle
Molecules 2010, 15(12), 8841-8855; doi:10.3390/molecules1512884

Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity

1
Laboratory of Applied Chemistry, Heterocycles, Fats and Polymers, Faculty of Science, University of Sfax, 3000 Sfax, Tunisia
2
Laboratory of Medicinal Chemistry of Natural Substances and Redox Pharmacophores, University of Toulouse, UPS, UMR 152, F-31062 Toulouse cedex 9, France
3
IRD, UMR 152, F-31062 Toulouse cedex 9, France
*
Author to whom correspondence should be addressed.
Received: 15 October 2010 / Revised: 25 November 2010 / Accepted: 30 November 2010 / Published: 3 December 2010
Download PDF [172 KB, uploaded 18 June 2014]

Abstract

In this paper we present the room temperature synthesis of a novel serie of 1,4-disubstituted-1,2,3-triazoles 4a-l by employing the (3 + 2) cycloaddition reaction of pyrimidinones containing alkyne functions with different model azides in the presence of copper sulphate and sodium ascorbate. To obtain the final triazoles, we also synthesized the major precursors 6-amino-5-cyano-1,4-disubstituted-2(1H)-pyrimidinones 3a-r from ethyl 2,2-dicyanovinylcarbamate derivatives 2a-c and various primary aromatic amines containing an alkyne group. The triazoles were prepared in good to very good yields.
Keywords: 2(1H)-pyrimidinones; 1,2,3-triazoles; (3 + 2) cycloaddition; alkynes; azides 2(1H)-pyrimidinones; 1,2,3-triazoles; (3 + 2) cycloaddition; alkynes; azides
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Najahi, E.; Sudor, J.; Chabchoub, F.; Nepveu, F.; Zribi, F.; Duval, R. Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity. Molecules 2010, 15, 8841-8855.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top