Issue 1, 2017

Divergent reactivity of α-azidochalcones with metal β-diketonates: tunable synthesis of substituted pyrroles and indoles

Abstract

A divergent reactivity of α-azidochalcones with metal β-diketonates for the synthesis of substituted pyrroles and indoles is described. Metal β-diketonates have been applied as bifunctional reactive partners. With a copper complex, the synthesis of substituted pyrroles in micellar media via 2H-azirine intermediates has been achieved under mild conditions, while with Fe(acac)2 as a catalyst, the reaction proceeds smoothly to yield indoles regioselectively.

Graphical abstract: Divergent reactivity of α-azidochalcones with metal β-diketonates: tunable synthesis of substituted pyrroles and indoles

Supplementary files

Article information

Article type
Research Article
Submitted
14 Sep 2016
Accepted
24 Oct 2016
First published
25 Oct 2016

Org. Chem. Front., 2017,4, 124-129

Divergent reactivity of α-azidochalcones with metal β-diketonates: tunable synthesis of substituted pyrroles and indoles

K. Rajaguru, A. Mariappan, S. Muthusubramanian and N. Bhuvanesh, Org. Chem. Front., 2017, 4, 124 DOI: 10.1039/C6QO00541A

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