Reactions of indole-2,3-dione 1 with 2-mercaptobenzimidazole, o-phenylenediamine, 2-
aminophenol, 2-aminobenzothiazole, 2-aminobenzimidazole and 3-methyl-1-phenyl-2-
pyrazolin-5-one were carried out to give compounds spiroindolethiazetobenzimidazole 2,
spirobenzimidazole(oxazole)indoline 3a,b, benzothiazol(imidazol) iminoindolinone 4a,b
and methyloxoindolylidenepyrazolone 5 respectively. Compound 5 was reacted with 2-
aminophenol as well as o-phenylenediamine to give new spirooxazepine and diazepine
derivatives 6a,b respectively. Reaction of 5 with nitrogen nucleophiles as well as carbon
nucleophiles was investigated to furnish new spiro heterocycles 7-11. The reaction of 2-(2-
oxo-1,2-dihydroindol-3-ylidene)malononitrile compound 12 with 3-methyl-1-phenyl-2-
pyrazoline-5-one was carried out to give spiroindolopyranopyrazolo derivative 13.
Compounds 4a,b was reacted with thioglycolic acid to give thiazolidinone derivatives
14a,b. Epoxidation of 5 using monoperoxyphthalic acid magnesium salt hexahydrate and
hydrogen peroxide were executed to afford the novel dispiro (2-pyrazolin
oxiraneindoline)dione compound 15. The chemical structures of the synthesized compounds
were well established by elemental and spectral analyses.