Reaction of pyrylium salts with nucleophiles. 23: Triarylethene derivatives containing an oxyalkyleneamino or oxyalkylene-N-pyridinium side chain
A synthetic design was devised for preparing primary amines related to anticancer drugs clomiphene and tamoxifen on the basis of key intermediates with a phenolic group, to which a side chain (ω-aminoethoxy or ω- aminopropoxy) was attached. These compound
Stanciuc,Balaban
p. 927 - 933
(2007/10/02)
Highly Stereoselective Access to an (E)-Vinyl Bromide from an Aryl Ketone Leads to Short Syntheses of (Z)-Tamoxifen and Important Substituted Derivatives
The enol triflate derived from a 1-(4-alkoxyphenyl)-2-phenyl-1-butanone is unstable, fragmenting to a vinyl cation that can be trapped by bromide ion.The E isomer of the vinyl bromide which is formed in preference (20:1) gave, upon palladium-catalyzed cou
Potter, Gerard A.,McCague, Raymond
p. 6184 - 6187
(2007/10/02)
The use of Octafluorotoluene and Pentafluoropyridine in the Synthesis of Pure Z and E Isomers of Derivatives of Tamoxifen -1-butene>
Octafluorotoluene and pentafluoropyridine have been used in the synthesis of pure Z and E isomers of derivatives of the anticancer drug, tamoxifen (1).The isomeric ethers derived by reaction of these perfluoroarenes with an E/Z mixture of 1,2-diphenyl-1-(4-hydroxyphenyl)-1-butene (3) and (4) were easily separated.A process is described for conversion of the E/Z mixtures into one isomer.Cleavage of the ethers regenerated the phenol (3) or (4) of pure stereochemical configuration and the Z-isomer (3) was used for the synthesis of tamoxifen (1) and various monomeric and dimeric analogues.Other perfluoroarenes were less useful.A short synthesis involving early introduction of the perfluorotolyl group is also described.
Jarman, Michael,McCague, Raymond
p. 1342 - 1388
(2007/10/02)
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