Modulating the reactivity of alpha -isocyanoacetates: multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones
2007
Résumé
The reactivity pattern of alpha -isocyanoacetates can be tuned by modulating the acidity of the alpha C-H bond(s) against the nucleophilicity of the conjugate base. Three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate (I) are described. E.g., reaction of I, morpholine, and cyclohexanal gave 92% 5-methoxyoxazole II. [on SciFinder (R)]
Détails
Titre
Modulating the reactivity of alpha -isocyanoacetates: multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones
Auteur(s)
Bonne, Damien ; Dekhane, Mouloud ; Zhu, Jieping
Publié dans
Angewandte Chemie, International Edition
Volume
46
Numéro
14
Pages
2485-2488
Date
2007
ISSN
1433-7851
Mots-clés (libres)
Aldehydes; Amines Role: RCT (Reactant); RACT (Reactant or reagent) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate; amines; and aldehydes); methoxyoxazole prepn; oxazole methoxy prepn; furopyrrolone prepn; nitrophenylisocyanoacetate reaction amine aldehyde
Note
CAN 147:30998
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
50-00-0 (Formaldehyde); 78-84-2 (Isobutanal); 91-21-4; 100-46-9 (Benzylamine); 100-52-7 (Benzaldehyde); 100-61-8 (N-Methylaniline); 104-53-0 (3-Phenylpropanal); 109-73-9 (Butylamine); 110-91-8 (Morpholine); 111-71-7 (Heptanal); 120-20-7; 122-78-1 (Benzeneacetaldehyde); 123-75-1 (Pyrrolidine); 350-46-9 (4-Fluoronitrobenzene); 506-59-2 (Dimethylamine hydrochloride); 637-44-5 (3-Phenylpropiolic acid); 2043-61-0 (Cyclohexanal); 39687-95-1 (Methyl alpha -isocyanoacetate); 135284-85-4; 939047-23-1; 939047-24-2 Role: RCT (Reactant), RACT (Reactant or reagent) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate); 7299-58-3P; 939047-03-7P; 939047-12-8P; 939047-22-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate); 939047-04-8P; 939047-05-9P; 939047-06-0P; 939047-07-1P; 939047-08-2P; 939047-09-3P; 939047-10-6P; 939047-11-7P; 939047-13-9P; 939047-14-0P; 939047-15-1P; 939047-16-2P; 939047-17-3P; 939047-18-4P; 939047-19-5P; 939047-20-8P; 939047-21-9P Role: SPN (Synthetic preparation), PREP (Preparation) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate)
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
50-00-0 (Formaldehyde); 78-84-2 (Isobutanal); 91-21-4; 100-46-9 (Benzylamine); 100-52-7 (Benzaldehyde); 100-61-8 (N-Methylaniline); 104-53-0 (3-Phenylpropanal); 109-73-9 (Butylamine); 110-91-8 (Morpholine); 111-71-7 (Heptanal); 120-20-7; 122-78-1 (Benzeneacetaldehyde); 123-75-1 (Pyrrolidine); 350-46-9 (4-Fluoronitrobenzene); 506-59-2 (Dimethylamine hydrochloride); 637-44-5 (3-Phenylpropiolic acid); 2043-61-0 (Cyclohexanal); 39687-95-1 (Methyl alpha -isocyanoacetate); 135284-85-4; 939047-23-1; 939047-24-2 Role: RCT (Reactant), RACT (Reactant or reagent) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate); 7299-58-3P; 939047-03-7P; 939047-12-8P; 939047-22-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate); 939047-04-8P; 939047-05-9P; 939047-06-0P; 939047-07-1P; 939047-08-2P; 939047-09-3P; 939047-10-6P; 939047-11-7P; 939047-13-9P; 939047-14-0P; 939047-15-1P; 939047-16-2P; 939047-17-3P; 939047-18-4P; 939047-19-5P; 939047-20-8P; 939047-21-9P Role: SPN (Synthetic preparation), PREP (Preparation) (three-component synthesis of 5-methoxyoxazoles and four-component synthesis of furopyrrolones involving Me alpha -(p-nitrophenyl)-alpha -isocyanoacetate)
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