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Report | Regular issue | Vol 16, No. 9, 1981, pp.1545-1553
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1545
■ Fluorine Containing Bioactive Heterocycles. Part III: Synthesis of Some New Fluorine Containing Phenylglyoxals and 1,2,4-Triazine Derivatives

Krishna C. Joshi,* Kalpana Dubey, and Anshu Dandia

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

Abstract

Some medicinally important new fluorine containing phenylglyoxals have been synthesized by selenium dioxide oxidation of appropriate fluorinated acetophenones and characterized by spectral studies. The phenylglyoxals were treated with thiosemicarbazide to give corresponding thiosemicarbazones (III) which were cyclized, in situ, to yield 5-(fluorophenyl)-1,2,4-triazine-3(2H)-thiones. The 5-(4-fluorophenyl)-1,2,4-triazine-3-(2)-thione (IV) undergoes nucleophilic displacement when refluxed with hydrazine hydrate to give corresponding 3-hydrazino-5-(4-fluorophenyl)-1,2,4-triazine. The hydrazino derivative reacts with fluorinated 1,3-diketones, in glacial acetic acid yielding 5-(4-fluorophenyl)-3-[1-(3,5-disubstituted)pyrazolyl]-1,2,4-triazines (VII). All synthesized compounds have been characterized on the basis of elemental analyses, ir, pmr and 19F nmr studies.