Stereospecific Reduction of 1,4,5,6-Tetrahydrobenzo[f]quinolin-3(2H)-ones with Triethylsilane-Trifluoroacetic Acid

Joseph G. Cannon; Karen S. Kirschbaum

doi:10.1055/s-1993-26018

Synthesis 1993; 1993(11): 1151-1154
DOI: 10.1055/s-1993-26018

paper

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Stereospecific Reduction of 1,4,5,6-Tetrahydrobenzo[f]quinolin-3(2H)-ones with Triethylsilane-Trifluoroacetic Acid

Joseph G. Cannon^* , Karen S. Kirschbaum

^*Division of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, Iowa City, Iowa 52242, USA

Abstract

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ß-Tetralone pyrrolidine enamines 6 react with acrylamine to produce mixtures of double bond positional isomeric tetrahydrobenzo[f] quinolin-3(2H)-ones, e.g. 3, 11, 12. Each of these isomers is reduced stereoselectively by triethylsilane-trifluoroacetic acid to the cis- or trans-fused octahydrobenzo[f]quinolone system, e. g. 4,5. It is established that reported failures to prepare pure trans-fused product 5 by this reductive method is due to the heterogeneity of the product of the ß-tetralone enamine-acrylamide reaction, and not to a defect in the reducing reagent system.

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