Sequential Knoevenagel [4+1] Cycloaddition–Condensation–Aza-Friedel–Crafts Intramolecular Cyclization: A 4-Center-3-Component Reaction Toward Tunable Fluorescent Indolizine Tetracycles

Nathan Bedard, Christopher Foley, Garrett J. Davis, John C. Jewett, Christopher Hulme

Research output: Contribution to journalArticlepeer-review

Abstract

A two-step multicomponent reaction oxidation protocol is reported herein, which affords novel tunable fluorescent tetracyclic indolizines. The procedure involves a novel 4-center-3-component reaction, which proceeds via a sequential Knoevenagel condensation, [4+1] cycloaddition, and imine condensation to afford imino-indolizines. Products then undergo cyclization and are oxidized in situ to afford fluorescent tetracycles, which are readily tunable through modification of diversity elements.

Original languageEnglish (US)
Pages (from-to)17550-17559
Number of pages10
JournalJournal of Organic Chemistry
Volume86
Issue number24
DOIs
StatePublished - Dec 17 2021

ASJC Scopus subject areas

  • Organic Chemistry

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