Razack Y. Synthesis and stereochemistry of partially hydrogenated 2H-indazoles

Investigation objects: derivatives of hexahydro-2H-indazole. Purpose: synthesis and stereochemisrty of partially hydrogenated N-aryl- and N-thiazolyl-2H-indazoles on the basis of reaction diarylidenecyclo-hexanones with arylhydrazines. Synthesis of N-thiazolyl hexahydro-2H-indazoles by the reaction of N-thiocarbomoylhexahydroindazoles with phenacetylhalogenide and chlorderivatives ?-dicarbonyl compounds are also worked out. A study has been made of the influence of the of substituents of these compounds on their stereochemistry, spectal and luminescence propertie. Methods: X-ray structural analysis, 1H NMR-, Masse- and IR-spectroscopy, absorption and fluorescence spectroscopy at stationary and pulse excitation, quantum chemical calculations. have been estimated. It has been shown that reaction of phenylhydrazines with 2,6-bis-benzylidene-cyclohexanones results in 3,3a-trans-2-phenyl-hexahydro-2H-indazoles, and along with this 1-phenyltetrahydro-[1H]indazoles are formed in a nomber of case. Atthe same time 3,3a-cis-2-phenylhexahydro-2H-indazoles were formed as major products in the reaction with 4-nitophenylhydrazine. In some cases, the heterocyclization is accompanied by a shift of the double bond in the pyrazoline ring.. Degree of application: design of new organic hexahydro-2H-indazoles as antimicrobial and luminophores agents.