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Paper | Regular issue | Vol 24, No. 9, 1986, pp.2479-2485
Published online, 1st January, 1970
DOI: 10.3987/R-1986-09-2479
Studies in Spiroheterocycles: Part IX: A New Elegant Synthesis and Reactions of Some Novel Fluorine-containing Spiro[3H-indole-3,2’-tetrahydro-1,3-thiazine]-2,4’(1H)-diones

Krishna C. Joshi,* Anshu Dandia, and Nidhal Ahmed

*Department of Chemistry, University of Rajasthan, Jaipur 302 004, India


A number of novel fluorine-containing spiro[3H-indole-3,2’-tetrahydro-1,3-thiazine]-2,4’(1H)-diones have been synthesized by an elegant one-step procedure involving the condensation of fluorine-containing indole-2,3-diones, fluorinated aromatic amines and 3-mercaptopropanoic acid without isolating the intermediate isatin-3-anils. The spiro compounds have been further subjected to acetylation, chloroacetylation and Mannich reactions. N-Acetylated spiro compound was simultaneously synthesized from 1-acetylindole-2,3-dione and aniline. The structures of all the compounds have been confirmed on the basis of elemental analyses, ir, 1H nmr, 13C nmr, 19F nmr and mass spectral studies.