Base-Promoted [4 + 1]/[3 + 1 + 1] Bicyclization for Accessing Functionalized Indeno[1,2-c]furans

Wen Juan Hao, Qian Gao, Bo Jiang, Feng Liu, Shu Liang Wang, Shu Jiang Tu, Guigen Li

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

A novel three-component bicyclization strategy for the metal-free synthesis of densely functionalized indeno[1,2-c]furans with generally good yields has been established from readily accessible o-phthalaldehydes (OPA), isocyanides, and α-diazoketones. The reaction pathway involves aldol-type addition, 1,2-hydride shift, 5-exo-trig cyclization, and 1,4-addition as well as an oxo-5-exo-dig cyclization sequence, resulting in continuous multiple bond-forming events including C-C and C-O bonds to rapidly build up functional oxo-heterocycles.

Original languageEnglish
Pages (from-to)11276-11281
Number of pages6
JournalJournal of Organic Chemistry
Volume81
Issue number22
DOIs
StatePublished - Nov 18 2016

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