The previously unknown 3 (4 chlorophenyl) 7,7 dimethyl 2 phenyl 3,3a,4,5,6,7 hexa hydroindazole 6a and (4 halophenyl) 7,7 dimethyl 1 phenyl 4,5,6,7 tetrahydroindazoles 7a,b were synthesized by the reaction of 6 arylidene 2,2 dimethylcyclohexanones with phenylhydr azine in the presence of pyridine. The molecular and crystal structures of compounds 7a,b were determined by X ray diffraction.Key words: 6 arylidene 2,2 dimethylcyclohexanones, 3 aryl 7,7 dimethyl 2 phenyl 3,3a,4,5,6,7 hexahydroindazoles, 3 aryl 7,7 dimethyl 2 phenyl 4,5,6,7 tetrahydroindazoles, X ray diffraction study, phenylhydrazine, cyclocondensation.Many drugs and biologically active compounds con tain pyrazole and pyrazoline moieties. In recent years, the biological activity of 3,3a,4,5,6,7 hexahydro 2(1H) ind azoles I and 3,3a,4,5 tetrahydro (2H) benz[g]indazoles II has received attention from researchers.Among hexahydroindazoles I, there are monoamine oxidase inhibitors having antidepressant properties 1-3 and antibacterial agents. 4-7 A series of substituted benz[g]ind azoles II are covered by patents as insecticides. 8,9 Earlier, we have found for the first time that new 2 thiocarbamoyl substituted (R 3 = CSNH 2 ) hexahydroindazoles I exhibit fungicidal activity against certain phytopathogenic fungi, and compounds containing one or two methyl groups in the 7 position (R 1 = H, R 2 = Me or R 1 = R 2 = Me) proved to be particularly active. 10,11 The conventional procedure for the synthesis of compounds I involves the nucleophilic addition of hydrazines or (thio)semicarbazides to 2 aryl idenecycloalkanones or 2,6 bis(arylidenecyclohexanones) followed by the cyclocondensation of the adduct. 12 In order to search for new fungicides, we continued our investigation of the cyclocondensation of 6 arylidene 2,2 dimethylcyclohexanones with 1,2 dinucleophiles by studying the reactions of these ketones with phenylhydr azine under different conditions.The reactions of phenylhydrazine with a series of 2,6 bis(arylidenecyclohexanones) 1 have been studied ear lier. 13 These reactions afforded hexahydroindazoles 2 as the major products along with dehydrogenated com pounds, viz., 1 phenyl substituted tetrahydroindazoles 3, as the minor products (Scheme 1). The structures of the latter were not established. 13 In this case, the 1 H NMR spectra were non informative; however, structure 3 was assigned to these compounds 13 based on indirect evidence by analyzing the results of the chemical transformations performed in the cited study. The oxidation of hexa hydroindazole 2 (Ar = Ph) with lead tetraacetate afforded isomeric 2 phenyltetrahydroindazole 4, the properties of which (m.p., the 1 H NMR spectrum) substantially differ from those of tetrahydroindazole 3 prepared by the con densation under consideration (see Scheme 1). However, the structures of phenyltetrahydroindazoles 3 have not been definitely proved in the study. 13 After the reaction of 6 unsubstituted 2 arylidene cyclohexanones with phenylhydrazine, the corresponding individual hexahydroindazoles were not...
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