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Type: Journal article
Title: The synthesis of tetrahydroquinolines related to virantmycin
Author: Francis, C.
Williamson, N.
Ward, A.
Citation: Synthesis: journal of synthetic organic chemistry, 2004; 16(16):2685-2691
Publisher: Georg Thieme Verlag KG
Issue Date: 2004
ISSN: 0039-7881
Abstract: 4-Substituted anilines react with 1-methoxymethyl-1-butyl-3- trimethysilylpropargyl chloride but not with 1,1-dibutyl-3- trimethylsilylpropargyl chloride, to form the corresponding substituted N-propargylanilines. These anilines cyclise, using cuprous chloride, in the presence of trifluoroacetic anhydride, and, when the aniline substituent is electron donating, to give 6-substituted 2-butyl-2-methoxymethyl-1- trifluoroacetyl-1,2-dihydroquinolines. Chlorination, followed by selective dechlorination using sodium cyanoborohydride, of the 6-methyl product yields 2-butyl-2-methoxymethyl-3-chloro-6-methyl-1-trifluoroacetyl-1,2,3, 4-tetrahydroquinoline which has the same relative stereochemistry as that in the antiviral compound, Virantmycin.
DOI: 10.1055/s-2004-831234
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Appears in Collections:Aurora harvest 2
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