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DOI: 10.1055/s-2004-831234
The Synthesis of Tetrahydroquinolines Related to Virantmycin
Publikationsverlauf
Publikationsdatum:
22. September 2004 (online)
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.
Key words
quinolines - diastereoselectivity - cyclisations - alkyl halides - alkynes - antiviral agents
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