A Decarboxylative C(sp3)−N Bond Forming Reaction to Construct 4-Imidazolidinones via Post-Ugi Cascade Sequence in One Pot

Gui Ting Song, Chuan Hua Qu, Jie Lei, Wei Yan, Dian Yong Tang, Hong yu Li, Zhong Zhu Chen, Zhi Gang Xu

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A post-Ugi one-pot cascade was developed to access 4-imidazolidinones through an intramolecular decarboxylative C(sp3)−N bond forming reaction. The reaction has a broad tolerance for a variety of substituted aldehydes, anilines, isocyanides and glyoxylic acids. The cascade reaction scope was expanded to synthesize spiroimidazolidinone by the replacement of aldehyde with aliphatic ketone in the Ugi reaction. Subsequently, the methodology was applied to synthesize the core structures of pharmaceuticals GSK2137305 and SCH 900822 under the mild and facile conditions with one purification. This cascade reaction generates opportunities for the tailored synthesis of a range of biologically active 4-imidazolidinones through tuneable Ugi inputs. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)4084-4091
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number19
DOIs
StatePublished - Oct 6 2020
Externally publishedYes

Keywords

  • 4-Imidazolidinones
  • Decarboxylation
  • Multicomponent reactions (MCRs)
  • One-pot
  • Spiroimidazolidinone

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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