Synthesis of some new spiro, isolated and fused heterocycles based on 1H-indole-2-one

The reaction of 3-benzoylcyanomethylidine-1(H)-indole-2-one (1) with a vari ety of active methylene compounds, thioglycolic acid, glycine, hydrazine hy drate and phenyl hydrazine led to the formation of compounds 4a-d-10. 3-Thi osemicarbazide-1 (H)-indole-2-one 2 on reaction with alpha -halocarbonyl co mpounds gave compounds 11a-c, 12a-c. The latter compounds on heating with p hosphoryl chloride, cyclization takes place via losing water to give the an gular tetracyclic compounds 13a,b and 14a-c. Cyanoacetic hydrazone derivati ve 3 readily cyclized upon heating in triethyl orthoformate to give the tri cyclic system, oxopyridazino indole 15. On the other hand, the reaction of 3 with benzylidine malononitrile and ben zylidene ethylcyanoactate gave the pyranyl hydrazone derivatives 16a,b.