Synthesis of alpha -keto amides by a molecular-sieves-promoted formal oxidative coupling of aliphatic aldehydes with isocyanides

The reaction of an aldehyde, an isocyanide, N-methylhydroxylamine, and acetic acid in the presence of 4-.ANG. mol. sieves afforded alpha -keto amides in moderate to good yields. In contrast, 3-.ANG. mol. sieves did not promote the desired multicomponent reaction. [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 47, 5, 947-950
Year:
2008
Keywords:
Note:
CAN 148:402630
21-2
General Organic Chemistry
Institut de Chimie de Substances Naturelles,CNRS,Gif-sue-Yvette Cedex,Fr.
Journal
1433-7851
written in English.
64-19-7 (Acetic acid); 104-53-0 (Benzenepropanal); 111-71-7 (Heptanal); 931-53-3 (Cyclohexyl isocyanide); 1930-94-5; 4229-44-1 (N-Methylhydroxylamine hydrochloride); 5949-05-3 ((S)-Citronellal); 7188-38-7 (tert.-Butyl isocyanide); 10340-91-7 (Benzyl isocyanide); 29601-98-7 (N-Benzylhydroxylamine hydrochloride); 33904-01-7 (3,4-Dimethoxyphenyl isocyanide); 39687-95-1 (Methyl isocyanoacetate); 57497-39-9 (N-tert.-Butylhydroxylamine hydrochloride); 63157-14-2; 66251-86-3; 98648-05-6; 107201-33-2; 1015255-66-9 Role: RCT (Reactant), RACT (Reactant or reagent) (synthesis of alpha -keto amides by a mol.-sieves-promoted formal oxidative coupling of aliph. aldehydes with isocyanides); 66251-87-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (synthesis of alpha -keto amides by a mol.-sieves-promoted formal oxidative coupling of aliph. aldehydes with isocyanides); 34633-21-1P; 66251-88-5P; 76399-69-4P; 345922-07-8P; 629648-27-7P; 1015255-63-6P; 1015255-64-7P; 1015255-65-8P; 1015255-67-0P; 1015255-68-1P; 1015255-69-2P; 1015255-70-5P; 1015255-71-6P; 1015255-72-7P; 1015255-73-8P; 1015255-74-9P; 1015255-75-0P; 1015255-76-1P Role: SPN (Synthetic preparation), PREP (Preparation) (synthesis of alpha -keto amides by a mol.-sieves-promoted formal oxidative coupling of aliph. aldehydes with isocyanides)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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