Use of α-Anilino Dienenitriles as Nucleophiles in Cycloadditions

Article abstract of DOI:10.1021/jo00263a040

The α-anilino dienenitriles 1-5 were prepared.The dienes 1-3 reacted with dichlorocarbene and electrophiles containing electron-deficient double bonds such as maleic anhydride, benzoquinone, dimethyl acetylenedicarboxylate, tetracyanoethylene, and chlorosulphonyl isocyanate.The diarylmethylamines 8-10, generated by cycloaddition of α-anilino dienenitriles and maleic anhydride, were successfully transformed into acridones 15-17.Intramolecular cyclization of trienes 4 and 5 yielded the carbazoles and dihydro derivatives, accompanied by formation of 2-cyano-1-methylindole.