SYNTHESIS AND REACTIONS OF 1-(4-CHLORO-, 3-CHLORO-, 2-CHLORO-, 2,4-DICHLORO-, AND 2,4-DIFLUOROPHENYL)-6,6-DIMETHYL-4-OXO-4,5,6,7-TETRAHYDROINDAZOLES

Abstract

Reaction of the potassium salt of 2-formyldimedone with hydrochlorides of 4-chloro-, 3-chloro-, 2-chloro-, 2,4-dichloro-, and 2,4-difluorophenylhydrazines gave the corresponding 2-arylhydrazinomethylene-dimedones which cyclized in acid media to 1-substituted 6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindazoles. Oxidation of the latter with selenious acid gave the corresponding 4,5-dioxo-4,5,6,7-tetrahydroindazoles which were further converted into 3-aryl-5,5-dimethyl-4,5-dihydro-3H-pyrazolo[4,3-a]phenazines and 2,6-diaryl-4,4-dimethyl-4,5-dihydro-1H(3H)-indazolo[4,5-g]imidazoles.

Authors: I. A. Strakova, A. Ya. Strakov, M. V. Petrova, and L. G. Delyatitskaya.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (4), pp 459-464

http://link.springer.com/article/10.1007/BF02269546