Metal-Free Synthesis of Pyrrolo[1,2-a]quinoxalines Mediated by TEMPO Oxoammonium Salts

Abstract We herein describe a novel TEMPO oxoammonium salt initiated Pictet–Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2- a ]quinoxalines or 5,6-dihydroindolo[1,2- a ]quin­oxalines in good to exc...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2018-07, Vol.50 (14), p.2727-2740
Main Authors: Huo, Heng-rui, Tang, Xiang-Ying, Gong, Yue-fa
Format: Article
Language:English
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Summary:Abstract We herein describe a novel TEMPO oxoammonium salt initiated Pictet–Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2- a ]quinoxalines or 5,6-dihydroindolo[1,2- a ]quin­oxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization–dehydrogenation process using one equivalent of the oxoammonium salt.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1610131