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■ 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

Abstract

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.