Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles

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

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides. The reaction pathway involves Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm rearrangement and an oxo-Diels-Alder reaction sequence, resulting in continuous multiple bond-forming events including C-N, C-O and C-H bonds to rapidly build up molecular complexity.

Original languageEnglish
Pages (from-to)900-903
Number of pages4
JournalChemical Communications
Volume52
Issue number5
DOIs
StatePublished - 2016

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