An expedient route to tricyanovinytindotes and indotylmateimides from o-alkynytanitines utilising DMSO as a one-carbon synthon

A Pd(II)/Cu(II) catalysed domino synthesis of tricyanovinylindoles has been achieved using DMSO as a onecarbon 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=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.

Automated summary

A Pd(II)/Cu(II) catalyzed domino synthesis of tricyanovinylindoles has been achieved using DMSO as a one-carbon synthon. The reaction involves the construction of 2-aryl-3-formyl indole, sequential addition of malononitrile and a CN to form multiple bonds, and post-synthetic modification resulting in the formation of 4-cyano-3-indolylmaleimides. Photophysical studies of selected compounds show emission in the visible range.