title: 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.affiliation: Laboratoire de Synthèse Organique Appliquée, Faculté des Sciences de l'Université, BP 1524 Es-Senia, Oran, 31000, Algeria.
authors.forename: Sarah
authors.initials: S
authors.lastname: Zeghada
authors.forename: Ghenia
authors.initials: G
authors.lastname: Bentabed-Ababsa
authors.forename: Aïcha
authors.initials: A
authors.lastname: Derdour
authors.forename: Safer
authors.initials: S
authors.lastname: Abdelmounim
authors.forename: Luis R
authors.initials: LR
authors.lastname: Domingo
authors.forename: José A
authors.initials: JA
authors.lastname: Sáez
authors.forename: Thierry
authors.initials: T
authors.lastname: Roisnel
authors.forename: Ekhlass
authors.initials: E
authors.lastname: Nassar
authors.forename: Florence
authors.initials: F
authors.lastname: Mongin
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001386:Azides / Q000737:chemistry*; D045744:Cell Line, Tumor; D003500:Cyclization; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013696:Temperature; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000475:Alkenes; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D001386:Azides; D014230:Triazoles