Abstract:
Malononitrile and its derivatives are essential components in the synthesis of many
organic heterocycles that are utilized in agricultural products, such as pesticides, and in
pharmaceutical chemicals. Recently, our laboratory has developed an efficient one-pot method to
synthesize 2-amino-4H-chromene-3-carbonitrile derivatives from malononitrile and
salicylaldehyde. In this method, 2-amino-4H-chromene-3-carbonitriles are created by reductive
alkylation through a Knoevenagel condensation and cyclization, which is followed by
subsequent conjugated reduction. The 2-amino-4H-chromene-3-carbonitrile derivatives can then
undergo standard alkylation conditions, such as methyl or allyl, resulting in opening of the
chromene heterocycle and formation of asymmetrically disubstituted malononitriles via slow Calkylation
which is followed by fast ring opining and O-alkylation.