Isoindole

Isoindole

Isoindole

Isoindole in heterocyclic chemistry is a benzo fused pyrrole. The compound is an isomer of indole and its reduced form is an isoindoline.

In solution the non-aromatic tautomer is predominant:

Isoindole tautomerism

and therefore the compound resembles a pyrrole more than a simple imine. Isoindoles are building blocks for phthalocyanines which are relevant as dyes

Isoindole-1,3-diones

The commercially important phthalimide is an isoindole-1,3-dione with two carbonyl groups attached to the heterocyclic ring. Thalidomide is an infamous drug based on this framework.

See also

• the structurally related isoindene with nitrogen replaced by a methylene group.