A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes.

Abstract

Reactions were performed from aryl azides on the one hand, and activated alkenes coming from β-dicarbonyl compounds or malonodinitrile on the other hand, either with recourse to conventional heating or to microwave activation, to afford 1-aryl-1H-1,2,3-triazoles. The mechanism and the regioselectivity of the reactions involving β-dicarbonyl compounds have been theoretically studied using DFT methods at the B3LYP/6-31G* level: they are domino processes comprising a tautomeric equilibrium of the β-dicarbonyl compounds with their enol forms, a 1,3-dipolar cycloaddition of the enol forms with the aryl azides (high activation energy), and a dehydration process (lower activation energy). The effect of non-conventional activation methods on the degradation of 1,2,3-triazolines was next studied experimentally. Finally, some of the 1,2,3-triazoles such synthesized were evaluated for their bactericidal and cytotoxic activities.

• Authors: Sarah Zeghada, Ghenia Bentabed-Ababsa, Aïcha Derdour, Safer Abdelmounim, Luis R Domingo, José A Sáez, Thierry Roisnel, Ekhlass Nassar, Florence Mongin
• Journal: Organic & biomolecular chemistry (Org Biomol Chem) Vol. 9 Issue 11 Pg. 4295-305 (Jun 07 2011) ISSN: 1477-0539 [Electronic] England
• PMID: 21494704 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkenes
• Anti-Bacterial Agents
• Antifungal Agents
• Antineoplastic Agents
• Azides
• Triazoles

Topics

• Alkenes (chemistry)
• Anti-Bacterial Agents (chemical synthesis, chemistry, pharmacology)
• Antifungal Agents (chemical synthesis, chemistry, pharmacology)
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Azides (chemistry)
• Cell Line, Tumor
• Cyclization
• Drug Screening Assays, Antitumor
• Humans
• Microbial Sensitivity Tests
• Microwaves
• Molecular Structure
• Quantum Theory
• Stereoisomerism
• Structure-Activity Relationship
• Temperature
• Triazoles (chemical synthesis, chemistry, pharmacology)