An expedient route to tricyanovinylindoles and indolylmaleimides from o-alkynylanilines utilising DMSO as a one-carbon synthon?

Organic & Biomolecular Chemistry Pub Date: 2021-07-20 DOI: 10.1039/D1OB01086G

Abstract

A Pd(II)/Cu(II) catalysed domino synthesis of tricyanovinylindoles has been achieved using DMSO as a one-carbon synthon. The reaction proceeds via the construction of 2-aryl-3-formyl indole followed by sequential addition of malononitrile and a CN resulting in two C–C, one C[double bond, length as m-dash]C and one C–N bonds in the final product. Furthermore, post-synthetic modification results in the unprecedented formation of 4-cyano-3-indolylmaleimides. Photophysical studies of selected compounds show emission in the visible range.

Graphical abstract: An expedient route to tricyanovinylindoles and indolylmaleimides from o-alkynylanilines utilising DMSO as a one-carbon synthon
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