Reaction of anthranilonitrile with some active methylene reagents: Synthesis of some new quinoline and quinazoline derivatives

Anthranilonitrile (1) reacts with ethyl cyanoacetate and its dimer, malononitrile, cyanothioacetamide and N-arylidene cyanoacetohydrazides 12a-c to afford pyrano[2,3-b]quinoline 5, cyanomethyl-quinazoline -10, pyrazolo[2,3-a]quinazoline 12 and triazolo[4,3-a]-quinoline derivatives 16a-c, respectively. Structures and conceivable mechanisms are discussed.