Download PDF
Synthesis 1993; 1993(11): 1151-1154
DOI: 10.1055/s-1993-26018
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
29 April 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.