Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to alpha -Ketoamides

Reaction of arom. aldehydes and isocyanides in the presence of N-methylhydroxyamine, acetic acid, and zinc chloride affords the aryl alpha -ketoamides, e.g. I, in moderate to good yields. [on SciFinder (R)]


Published in:
Journal of Organic Chemistry, 75, 8, 2748-2751
Year:
2010
Keywords:
Note:
CAN 152:380994, 25-16, Benzene, Its Derivatives, and Condensed Benzenoid Compounds, Centre de Recherche de Gif,Institut de Chimie des Substances Naturelles,Gif-sur-Yvette Cedex,Fr., Journal, 0022-3263, written in English., 1218939-18-4P Role: SPN (Synthetic preparation), PREP (Preparation) (Passerini reaction of aryl alpha -ketoamide with tert-Bu isocyanide); 935764-11-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of aryl primary alpha -ketoamide); 66-99-9 (2-Naphthylcarboxaldehyde); 99-61-6 (3-Nitrobenzaldehyde); 100-52-7 (Benzaldehyde); 104-87-0 (4-Methylbenzaldehyde); 104-88-1 (4-Chlorobenzaldehyde); 122-03-2 (4-Isopropylbenzaldehyde); 123-11-5 (4-Methoxybenzaldehyde); 529-20-4 (2-Methylbenzaldehyde); 587-04-2 (3-Chlorobenzaldehyde); 620-23-5 (3-Methylbenzaldehyde); 2769-71-3; 3132-99-8 (3-Bromobenzaldehyde); 7188-38-7 (tert-Butyl isocyanide); 10340-91-7 (Benzyl isocyanide); 14542-93-9; 21872-32-2; 22110-53-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); 64-19-7 (Acetic acid) Role: RCT (Reactant), RGT (Reagent), RACT (Reactant or reagent) (prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); 935764-19-5P; 1218939-15-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); 4229-44-1 (N-Methylhydroxylamine hydrochloride); 7646-85-7 (Zinc chloride) Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); 21010-60-6P; 28193-70-6P; 69725-02-6P; 69770-99-6P; 95725-10-3P; 95725-11-4P; 1218939-10-6P; 1218939-11-7P; 1218939-12-8P; 1218939-13-9P; 1218939-14-0P; 1218939-16-2P; 1218939-17-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); 111-71-7 (Heptanal) Role: RCT (Reactant), RACT (Reactant or reagent) (zinc chloride-promoted formal oxidative coupling and Passerini reaction of aliph. aldehyde and tert-Bu isocyanide); 34633-21-1P; 1218939-09-3P Role: SPN (Synthetic preparation), PREP (Preparation) (zinc chloride-promoted formal oxidative coupling and Passerini reaction of aliph. aldehyde and tert-Bu isocyanide)
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 Record created 2010-11-25, last modified 2018-03-17


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