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Reactions of fluorinated 3-(2-oxocycloalkylidene)indol-3(1H)-ones (1) with 4-fluorophenylsulphonyl hydrazide in ethanolic KOH yielded spiro[3H-indazole-3,3′(3H)-indole]-2′(1’H)-ones (2a, b; n = 2) and spiro[3H-indole-3,3′(3H)-pyrazol]-2(1H)-ones (2c; n = 1). Further, the reaction of 1 with hydroxylamine hydrochloride in dry pyridine in the presence of fused sodium acetate yielded some new 2,3a,4,5,6,7-hexahydro[spiro-3H-benzisoxazole-3,3′(3H)-indol]-2′(1’H)-ones (3a, b; n = 2) and 4′,5′-cyclopentaspiro[3H-indole-3,3′(3H)-isoxaazol]-2(1H)-ones (3c, d; n = 1). The nonfluorinated analog gave 3-(2-oxocycloalkylidene)-2′-oximeindole-2(1H)-one (4a) in addition to the spiro compound (3a). All the compounds have been characterised from their analytical and ir, pmr, C-13 nmr, F-19 nmr and mass spectral data.
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Reference:
Benzisoxazole – Wikipedia,
,Benzisoxazole – an overview | ScienceDirect Topics