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)]


Published in:
Angewandte Chemie, International Edition, 45, 21, 3495-3497
Year:
2006
Keywords:
Note:
CAN 145:166655
21-2
General Organic Chemistry
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1433-7851
written in English.
60-12-8 (2-Phenylethanol); 65-85-0 (Benzoic acid); 71-36-3 (1-Butanol); 100-51-6 (Benzyl alcohol); 931-53-3 (Cyclohexyl isonitrile); 1138-80-3; 1161-13-3; 3966-32-3; 7188-38-7 (tert-Butyl isonitrile); 10340-91-7 (Benzyl isonitrile); 17996-12-2; 26164-26-1; 39687-95-1 (Methyl isocyanoacetate); 52485-50-4; 52485-51-5; 55036-19-6; 68750-24-3 (6-Acetoxy-1-hexanol); 77987-49-6 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid); 64297-64-9 (o-Iodoxybenzoic acid) Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid); 89881-22-1P; 132505-08-9P; 237057-79-3P; 901765-08-0P; 901765-09-1P; 901765-10-4P; 901765-11-5P; 901765-12-6P; 901765-13-7P; 901765-14-8P; 901765-15-9P; 901765-16-0P; 901765-17-1P; 901765-18-2P; 901765-19-3P; 901765-20-6P; 901765-21-7P; 901765-22-8P; 901765-23-9P; 901765-24-0P; 901765-25-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid)
Laboratories:




 Record created 2010-11-25, last modified 2018-01-28


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