Base-promoted transannulation of heterocyclic enamines and 2,3-epoxypropan-1-ones: Regio- and stereoselective synthesis of fused pyridines and pyrroles

Zheng Yang, Wen Juan Hao, Hai Wei Xu, Shu Liang Wang, Bo Jiang, Guigen Li, Shu Jiang Tu

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Base-promoted transannulation of heterocyclic enamines and 2,3-epoxypropan-1-ones has been successfully achieved, providing a new access to structurally diverse fused pyridines and pyrroles with excellent regio- and stereoselectivity. Treatment with N-aryl 4-aminofuran-2(5H)-ones and 2,3-epoxypropan-1-ones under microwave heating resulted in functional furo[3,2-b]pyridines in good yields. The N-aryl 4-aminopyrrol-2(5H)-ones bearing an electron-withdrawing group engaged in the reaction afforded pyrrolo[3,2-b]pyridines, whereas their counterparts with an electron-neutral or an electron-donating group underwent a different reaction pathway to form pyrrolo[3,2-b]pyrroles through C-C bond cleavage.

Original languageEnglish
Pages (from-to)2781-2789
Number of pages9
JournalJournal of Organic Chemistry
Volume80
Issue number5
DOIs
StatePublished - Mar 6 2015

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