Monosubstituted Oxazoles. 1. Synthesis of 5-Substituted Oxazoles by Directed Alkylation
A general method is presented for synthesis of 2-(methylthio)-5-substituted oxazoles 2. Deprotonation of the readily available 2-(methylthio)oxazole (1) with n-BuLi occurs smoothly in the presence of TMEDA and regiospecifically at C5. The organometallic 1a added rapidly to aldehydes and other electrophiles to provide 5-substituted-2-(methylthio)oxazoles in very good to excellent yields. Reductive removal of the MeS group gave the desired 5-monosubstituted oxazoles 3 in good yield.
The invention relates to 2-(benzylsulfonyl)-oxazole derivatives, chiral 2-(benzylsulfinyl)-oxazole derivatives and 2-(benzylsulfanyl)-oxazole derivatives of general formula (I) and the salts thereof, wherein the individual radicals and indexes have the me
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Page/Page column 25
(2011/08/08)
Nickel-catalyzed synthesis of oxazoles via C-S activation
The synthesis of 2-substituted oxazoles is achieved via nickel-catalyzed cross-coupling reaction of 2-methylthio-oxazole and various organozinc reagents. An extension of this method is demonstrated with a chemoselective, one-pot synthesis of unsymmetrical
Lee, Kyoungsoo,Counceller, Carla M.,Stambuli, James P.
supporting information; experimental part
p. 1457 - 1559
(2009/08/08)
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