57134-36-8Relevant articles and documents
New general synthesis of α-alkoxyketones via α′- alkylation, α-alkylation and α,α′-dialkylation of α-alkoxyketimines
Colpaert, Filip,Mangelinckx, Sven,Rocchetti, Maria Teresa,De Kimpe, Norbert
experimental part, p. 549 - 558 (2011/02/28)
α-Methoxy- and α-ethoxyketones, as important intermediates in organic synthesis and flavor compounds in food chemistry, were synthesized by deprotonation of N-(1-alkoxy-2-propylidene)isopropylamine, prepared by condensation of the corresponding α-alkoxyacetone with isopropylamine, and subsequent reaction of the corresponding 1-azaallylic anions with alkyl halides to afford α′-alkylated, α-alkylated and α, α′-dialkylated ketimines. Hydrolysis of the imino function led to the desired substituted α-alkoxyketones. The ratio of α-, α′-, and α,α′-(di)alkylated compounds depended on the amount of base used and on the nature of the alkylating reagent.
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.
