title: One-Pot Synthesis of Imidazole-4-Carboxylates by Microwave-Assisted 1,5-Electrocyclization of Azavinyl Azomethine Ylides.
abstract: Diversely functionalized imidazole-4-carboxylates were synthesized by microwave-assisted 1,5-eletrocyclization of 1,2-diaza-1,3-diene-derived azavinyl azomethine ylides. 1,2-Diaza-1,3-dienes were treated with primary aliphatic or aromatic amines and subjected to microwave irradiation in the presence of aldehydes. 3-Alkyl- and 3-arylimidazole-4-carboxylates were prepared in good yields through a one-pot multicomponent procedure. Modulation of the substituents at C-2, N-3 and C-5 was possible, and 2-unsubstituted imidazoles were obtained when paraformaldehyde was used.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, Via Campi 183, 41100 Modena, Italy.
authors.forename: Lisa
authors.initials: L
authors.lastname: Preti
authors.forename: Orazio A
authors.initials: OA
authors.lastname: Attanasi
authors.forename: Emilia
authors.initials: E
authors.lastname: Caselli
authors.forename: Gianfranco
authors.initials: G
authors.lastname: Favi
authors.forename: Claudia
authors.initials: C
authors.lastname: Ori
authors.forename: Paolo
authors.initials: P
authors.lastname: Davoli
authors.forename: Fulvia
authors.initials: F
authors.lastname: Felluga
authors.forename: Fabio
authors.initials: F
authors.lastname: Prati
keywords: Azomethine ylides; Electrocyclic reactions; Microwave chemistry; Multicomponent reactions; Nitrogen heterocycles