Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to alpha -Ketoamides
2010
Résumé
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)]
Détails
Titre
Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to alpha -Ketoamides
Auteur(s)
Bouma, Marinus ; Masson, Geraldine ; Zhu, Jieping
Publié dans
Journal of Organic Chemistry
Volume
75
Numéro
8
Pages
2748-2751
Date
2010
Mots-clés (libres)
Aldehydes Role: RCT (Reactant); RACT (Reactant or reagent) (arom.; prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); Coupling reaction (oxidative; prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); Amides Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (oxo; prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); Reaction mechanism (prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); Isocyanides Role: RCT (Reactant); RACT (Reactant or reagent) (prepn. of aryl alpha -ketoamides via zinc chloride-promoted formal oxidative coupling of arom. aldehydes and isocyanides); aryl ketoamide prepn mechanism; arom aldehyde isocyanide formal oxidative coupling zinc chloride promoted
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)
Laboratoires
LSPN
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LSPN - Laboratoire de synthèse et produits naturels
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Date de création de la notice
2010-11-25