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One‐Pot Synthesis of Imidazole‐4‐Carboxylates by Microwave‐Assisted 1,5‐Electrocyclization of Azavinyl Azomethine Ylides
Author(s) -
Preti Lisa,
Attanasi Orazio A.,
Caselli Emilia,
Favi Gianfranco,
Ori Claudia,
Davoli Paolo,
Felluga Fulvia,
Prati Fabio
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000434
Subject(s) - chemistry , imidazole , microwave , organic chemistry , combinatorial chemistry , quantum mechanics , physics
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.