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Selective construction of functionalized chromeno[3,4-b]pyrroles and benzo[c]chromenes via a K3PO4 promoted three-component reaction

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Abstract

An efficient and convenient synthetic protocol for functionalized chromeno[3,4-b]pyrroles was successfully developed through a K3PO4 promoted three-component reaction of pivaloylacetonitrile (benzoylacetonitrile), dialkyl but-2-ynedioates and 2-aryl-3-nitrochromenes in refluxing ethyl acetate. A similar three-component reaction of malononitrile, dialkyl but-2-ynedioates and 2-aryl-3-nitrochromenes resulted in polysubstituted benzo[c]chromene derivatives in good yields. Plausible reaction mechanisms for selective formation of two annulated chromanes were rationally proposed.

Graphical abstract: Selective construction of functionalized chromeno[3,4-b]pyrroles and benzo[c]chromenes via a K3PO4 promoted three-component reaction

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Article information


Submitted
14 Nov 2019
Accepted
01 Mar 2020
First published
02 Mar 2020

New J. Chem., 2020, Advance Article
Article type
Paper

Selective construction of functionalized chromeno[3,4-b]pyrroles and benzo[c]chromenes via a K3PO4 promoted three-component reaction

W. Jiang, J. Sun and C. Yan, New J. Chem., 2020, Advance Article , DOI: 10.1039/C9NJ05693A

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