Diversely functionalized imidazole-4-carboxylates were synthesizedby 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 aromaticamines and subjected to microwave irradiation in thepresence of aldehydes. 3-Alkyl- and 3-arylimidazole-4-carboxylateswere prepared in good yields through a one-potmulticomponent procedure. Modulation of the substituentsat C-2, N-3, and C-5 was possible, and 2-unsubstituted imidazoleswere obtained when paraformaldehyde was used
One-Pot Synthesis of Imidazole-4-Carboxylates by Microwave-Assisted 1,5-Electrocyclization of Azavinyl Azomethine Ylides / Preti, L.; Attanasi, O. A.; Caselli, E.; Favi, G.; Ori, C.; Davoli, P.; Felluga, Fulvia; Prati, F.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2010:(2010), pp. 4312-4320. [10.1002/ejoc.201000434]
One-Pot Synthesis of Imidazole-4-Carboxylates by Microwave-Assisted 1,5-Electrocyclization of Azavinyl Azomethine Ylides
FELLUGA, FULVIA;
2010-01-01
Abstract
Diversely functionalized imidazole-4-carboxylates were synthesizedby 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 aromaticamines and subjected to microwave irradiation in thepresence of aldehydes. 3-Alkyl- and 3-arylimidazole-4-carboxylateswere prepared in good yields through a one-potmulticomponent procedure. Modulation of the substituentsat C-2, N-3, and C-5 was possible, and 2-unsubstituted imidazoleswere obtained when paraformaldehyde was usedPubblicazioni consigliate
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