Synthesis of imidazoles via cascade reaction of nitroallylic acetates with amidines and studies on their trypanocidal activity

Kumar, Tarun ; Verma, Deepti ; Menna-Barreto, Rubem F. S. ; Valença, Wagner O. ; da Silva Júnior, Eufrânio N. ; Namboothiri, Irishi N. N. (2015) Synthesis of imidazoles via cascade reaction of nitroallylic acetates with amidines and studies on their trypanocidal activity Organic and Biomolecular Chemistry, 13 (7). pp. 1996-2000. ISSN 1477-0520

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Official URL: http://doi.org/10.1039/c4ob02561j

Related URL: http://dx.doi.org/10.1039/c4ob02561j

Abstract

A one-pot, two step synthesis of highly substituted imidazoles has been carried out in good to excellent yields for the first time via a cascade intermolecular aza-SN2′-intramolecular aza-Michael addition involving a variety of Morita-Baylis-Hillman acetates of nitroalkenes and amidines in the presence of DABCO at room temperature. The synthetic and biological utility of the products has been demonstrated. In particular, some of the imidazoles exhibited potent activity against T. cruzi, the etiological agent of Chagas disease.

Item Type:Article
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ID Code:121334
Deposited On:14 Jul 2021 11:24
Last Modified:14 Jul 2021 11:24

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