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■ Reactions of 3-Hydrazino-5H-1,2,4-triazino[5,6-b]indoles with Trifluoroacetic Anhydride, Acetylacetone, Hexafluoroacetylacetone and Acetophenone

Krishna C. Joshi* and Pooran Chand

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

Abstract

3-Hydrazino-5H-1,2,4-triazino[5,6-b]indole affords a tetracyclic ring system containing compound: 3-trifluoromethyl-10H-1,2,4-triazolo[4’,3’:2,3][1,2,4]triazino[5,6-b]indole with trifluoroacetic anhydride. 3-Hydrazino derivatives, react with acetylacetone, in absolute ethanol giving rise to 3-[1-(3,5-dimethylpyrazolyl)]-5H-1,2,4-triazino[5,6-b]indoles while the reaction with hexafluoroacetylacetone gives ccrresponding hydrazone instead of expected 3-[1-(3,5-bis(trifluoromethyl)pyrazolyl)]-5H-1,2,4-triazino[5,6-b]indole. 3-Hydrazino derivatives also condense with acetophenone but the resulting hydrazone does not produce thiazolidinone with mercaptoacetic acid. All the synthesized compounds have been characterized on the basis of elemental analyses and ir, pmr, ¹⁹F nmr and mass spectral studies.