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Paper | Regular issue | Vol 31, No. 3, 1990, pp.473-477
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5133
Studies in Sprioheterocycles: Part XXVIII: Investigation of the Reaction of 3-Aroylmethyleneindolin-2-ones with Thiosemicarbazide and Synthesis of Spiro[3H-indole-3.4’(3’H)-pyrimidin]-2(1H)-ones

Krishna C. Joshi, Renuka Jain, and Kanti Sharma*

*Department of Chemistry, R. L. Saharia Govt. College, Kaladera, Jaipur 302 004, India

Abstract

Simple and N-substituted 3-aroylmethyleneindolin-2-ones (IV) have been obtained by the reaction of indole-2,3-diones with methyl ketones followed by dehydration. The reaction of IV with thiosemicarbazide has been investigated to study the effect of substitution on N atom. Our studies revealed that IV (R=H), on reaction with thiosemicarbzide, afforded exclusively the hydrazone (V) but under exactly limilar conditions, N-methyl-3-aroylmethyleneindolin-2-ones (IV; R=CH3) afforded spiro[3H-indole-3,4’(3’H)-pyrimidin]-2(1H)-ones (IV).