Dieckmann Condensation of Ugi N-Acylamino Amide Product: Facile Access to Functionalized 2,2-Disubstituted Indolin-3-ones

Yong Li, Jia Xu, Liu Jun He, Ya Fei Luo, Jiang Ping Meng, Dian Yong Tang, Hong Yu Li, Zhong Zhu Chen, Zhi Gang Xu

Research output: Contribution to journalArticlepeer-review

Abstract

Structurally unique 2,2-disubstituted indolin-3-ones with a quaternary carbon center have been constructed through a novel C-C bond formation at the C3 position of Ugi N-acylamino amide adducts employing an organic base-mediated Dieckmann condensation. This facile, flexible protocol can be fine-tuned to construct drug-like pyrazino[1,2-a]indole fragments with the same quaternary carbon center only through the variation of the acid part in Ugi input. This novel and expeditious methodology has a broad scope and can rapidly generate the drug-like indolin-3-one core.

Original languageEnglish (US)
Pages (from-to)823-834
Number of pages12
JournalJournal of Organic Chemistry
Volume87
Issue number1
DOIs
StatePublished - Jan 7 2022

ASJC Scopus subject areas

  • Organic Chemistry

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