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Report | Regular issue | Vol 19, No. 8, 1982, pp.1453-1461
Published online, 1st January, 1970
DOI: 10.3987/R-1982-08-1453
Tetracyclic Phenothiazines. VIII. Metal Hydride Reductions of Some 1,2-Dihydro-3-keto-3H-pyrido[3,2,1-kl]phenothiazines

Lal C. Vishwakarma, Vidyadhar M. Paradkar, Arnold R. Martin, and Cor J. Grol

*Department of Pharmaceutical Sciences, College of Pharmacy, The University of Arizona, Tucson, AZ 85721, U.S.A.

Abstract

Aluminum hydride (alane) in ether reduces 1,2-dihydro-3-keto-3H-pyrido[3,2,1-kl]phenothiazines bearing hydrogen, thioether or dimethylaminomethyl substituents at the 2-position to the respective hydrocarbons. In the corresponding 2-carbethoxy derivative (a β-ketoester), the ester group is reduced to a hydroxymethyl or methyl function depending on the amount of reagent and its mode of generation. Reductions with borane in tetrahydrofuran afford mixtures of the corresponding hydrocarbons, alcohols and occasionally alkenes in varying amounts depending on the nature of the 2-substituent.