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Alcohols in isonitrile-based multicomponent reaction: Passerini reaction of alcohols in the presence of o-iodoxybenzoic acid

An alc. instead of an aldehyde was found to be an effective reaction partner in the three-component Passerini reaction (P-3CR) in the presence of o-iodoxybenzoic acid (IBX). Thus, by simply heating a soln. of an alc. R1CH2OH [R1 = n-Pr, Ph, PhCH2, AcO(CH2)5, PhCH2OCONHCH2, (R)-AcNHCH(CH2Ph), etc.], a carboxylic acid R2CO2H [R2 = Me, Ph, (S)-MeOCHPh, etc.], an isonitrile R3NC (R3 = Me3C, MeO2CCH2, cyclohexyl, PhCH2), and IBX at 40 DegC, an oxidn./P-3CR sequence occurred smoothly to afford the corresponding alpha -acyloxy carboxamides R2CO2CHR1CONHR3 in good to excellent yields. [on SciFinder (R)]

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