66031-35-4Relevant academic research and scientific papers
The synthesis of tetrahydroquinolines related to Virantmycin
Francis, Craig L.,Williamson, Natalie M.,Ward, A. David
, p. 2685 - 2691 (2007/10/03)
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.
A NEW SYNTHETIC METHOD FOR 1-METHOXY-2-ALKANONES FROM 1,2-DIMETHOXYETHENYLLITHIUM AND ORGANOBORANES
Koshino, Junji,Sugawara, Takahiro,Yogo, Toshinobu,Suzuki, Akira
, p. 933 - 934 (2007/10/02)
1-Methoxy-2-alkanones are prepared from ate-complexes formed from 1,2-dimethoxyethenyllithium and trialkylboranes by the reaction with BF3*Et2O, followed by basic hydrogen peroxide oxidation.
