Regioselective synthesis of 2-amino-isophthalonitriles through a ring transformation strategy

Abstract

An expeditious synthesis of several 2-amino-isophthalonitriles and their biaryl compounds is described and illustrated by carbanion-induced ring transformation of functionalized 2H-pyran-2-ones with malononitrile in excellent yields. The strength of the reaction lies in the creation of an aromatic ring at room temperature from six-membered lactones under mild reaction conditions. This approach is an alternative to Diels–Alder reactions of 2H-pyran-2-ones with dienophiles, which require forcing thermal conditions to obtain benzene derivatives.