(Z)-Stereoselective Synthesis of Mono- and Bis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction

Zhigang Xu, Guillermo Martinez-Ariza, Alexandra P. Cappelli, Sue A Roberts, Christopher Hulme

Research output: Contribution to journalArticle

21 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)9007-9015
Number of pages9
JournalJournal of Organic Chemistry
Volume80
Issue number18
DOIs
StatePublished - Sep 18 2015

ASJC Scopus subject areas

  • Organic Chemistry

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