title: Synthesis of imidazoles via cascade reaction of nitroallylic acetates with amidines and studies on their trypanocidal activity.
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.
authors.affiliation: Indian Institute of Technology Bombay, Mumbai 400 076, India. irishi@iitb.ac.in.
authors.forename: Tarun
authors.initials: T
authors.lastname: Kumar
authors.forename: Deepti
authors.initials: D
authors.lastname: Verma
authors.forename: Rubem F S
authors.initials: RF
authors.lastname: Menna-Barreto
authors.forename: Wagner O
authors.initials: WO
authors.lastname: Valença
authors.forename: Eufrânio N
authors.initials: EN
authors.lastname: da Silva Júnior
authors.forename: Irishi N N
authors.initials: IN
authors.lastname: Namboothiri
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000578:Amidines / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D010654:Phenylbutyrates / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014349:Trypanosoma cruzi / Q000187:drug effects*
chemical_list: D000085:Acetates; D000578:Amidines; D007093:Imidazoles; D010654:Phenylbutyrates; D014344:Trypanocidal Agents