5 -Oxazolones electrochemical reduction

Treatment of 4-methoxy-2-oxazolidinone 86 with indolylmagnesium bromide 87, followed by A-protection with a ferf-butoxycarbonyl (Boc) group affords NJd -di-Boc-4-(3-indolyl)-2-oxazolidinone 88. Subsequent treatment with A-bromosuc-cinimide (NBS) in the presence of azobisisobutyronitrile (AIBN) followed by electrochemical reduction yields the protected 4-(3-indolyl)-2(3//)-oxazolone 90 (Fig. 5.23). The Boc groups are easily removed by pyrolysis."" "" ... [Pg.14]

Electrochemical reduction of 4-benzylidene-2-methyl-5(47/)-oxazolone to produce racemic Al-acetylphenylalanine has been accomplished using lead and cadmium cathodes. ... [Pg.282]

The electrochemical reduction of oxazolones was used for the synthesis of substituted phenylalanines 416) ... [Pg.47]

Oxazolone itself can be easily obtained from oxazolidinone through electrochemical reduction as described in CHEC-II(1996). A similar sequence was utilized in the synthesis of indole-substituted 2(3//)-oxazolone 244 (Scheme 71) <1997CPB733>. Electrochemical oxidation of 2-oxazolidinone in methanol gave a 4-methoxy oxazolidinone 241, which reacted with an organomagnesium indole reagent 242 in the presence of BF3-Et20, followed by... [Pg.526]

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