title: (Z)-Stereoselective Synthesis of Mono- and Bis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction.
abstract: Several novel cascade reactions are herein reported that enable access to a variety of unique mono- and bis-heterocyclic scaffolds. The sequence of cascade events are mediated through acid treatment of an Ugi adduct that affords 1,5-benzodiazepines which subsequently undergo an elegant rearrangement to deliver (E)-benzimidazolones, which through acid-promoted tautomerization convert to their corresponding (Z)-isomers. Moreover, a variety of heterocycles tethered to (Z)-benzimidazole-2-ones are also accessible through similar domino-like processes, demonstrating a general strategy to access significantly new scaffold diversity, each containing four points of potential diversification. Final structures of five scaffolds have been definitively proven by X-ray crystallography.
authors: Biological Sciences West Room 351, Department of Pharmacology and Toxicology, College of Pharmacy, The University of Arizona , 1041, East Lowell Street, Tucson, Arizona 85721, United States.
authors: Zhigang
authors: Z
authors: Xu
authors: Biological Sciences West Room 351, Department of Pharmacology and Toxicology, College of Pharmacy, The University of Arizona , 1041, East Lowell Street, Tucson, Arizona 85721, United States.
authors: Guillermo
authors: G
authors: Martinez-Ariza
authors: Biological Sciences West Room 351, Department of Pharmacology and Toxicology, College of Pharmacy, The University of Arizona , 1041, East Lowell Street, Tucson, Arizona 85721, United States.
authors: Alexandra P
authors: AP
authors: Cappelli
authors: Department of Chemistry and Biochemistry, The University of Arizona , Tucson, Arizona 85721, United States.
authors: Sue A
authors: SA
authors: Roberts
authors: Biological Sciences West Room 351, Department of Pharmacology and Toxicology, College of Pharmacy, The University of Arizona , 1041, East Lowell Street, Tucson, Arizona 85721, United States.|Department of Chemistry and Biochemistry, The University of Arizona , Tucson, Arizona 85721, United States.
authors: Christopher
authors: C
authors: Hulme
mesh_terms: D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001562:Benzimidazoles; D006571:Heterocyclic Compounds; C053110:benzimidazol-2-one