Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure
2002
Résumé
Novel three-component domino processes to polyheterocycles are developed. Reaction of an allylamine, an aldehyde and an alpha -isocyanoacetamide in methanol at room temp. provides an efficient access to an oxa-bridged tricycle as a single diastereoisomer. In this one-pot process, one C-N, one C-O and three C-C bonds are formed with concomitant creation of five asym. centers. While isolable, the oxa-bridged tricycles can be cleanly in-situ fragmented to pyrrolopyridines under acidic conditions (trifluoroacetic acid, -78 DegC), providing thus an unusual work-up derived structural diversity. The operational simplicity and excellent chem. yield make these novel heterocycle syntheses valuable in diversity-oriented high throughput synthesis. [on SciFinder (R)]
Détails
Titre
Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure
Auteur(s)
Gamez-Montano, Rocio ; Gonzalez-Zamora, Eduardo ; Potier, Pierre ; Zhu, Jieping
Publié dans
Tetrahedron
Volume
58
Numéro
32
Pages
6351-6358
Date
2002
ISSN
0040-4020
Mots-clés (libres)
Macrocyclic compounds Role: SPN (Synthetic preparation); PREP (Preparation) (nitrogen-oxygen; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); Fragmentation reaction (prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); Addition reaction (stereoselective; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); oxo bridged polyheterocycle prepn multicomponent domino process; pyrrolopyridines oxo bridged prepn multicomponent domino process; diastereoisomeric oxo bridged polyheterocycle pyrrolopyridines multicomponent domino process
Note
CAN 138:73220
28-15
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
written in English.
479666-46-1P Role: SPN (Synthetic preparation), PREP (Preparation) (intermediate; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 479666-39-2P; 479666-40-5P; 479666-41-6P; 479666-42-7P; 479666-43-8P; 479666-44-9P; 479666-45-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 479666-49-4P; 479666-50-7P; 479666-51-8P; 479666-52-9P; 479666-53-0P; 479666-54-1P; 479666-55-2P; 479666-56-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 129975-11-7 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with aldehyde and isocyanoacetamide; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 124-02-7 (Diallyl amine); 136142-48-8; 479666-47-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with aldehyde and isonitrile; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 479666-38-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with allylamine and aldehyde; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 111-71-7 (Heptanal) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with allylamine and isocyanoacetamide; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 1440-28-4; 479666-48-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with amine and aldehyde; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 104-53-0 (Benzenepropanal); 6688-11-5 (Cyclooctanecarboxaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with amine and isonitrile; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes)
28-15
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
written in English.
479666-46-1P Role: SPN (Synthetic preparation), PREP (Preparation) (intermediate; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 479666-39-2P; 479666-40-5P; 479666-41-6P; 479666-42-7P; 479666-43-8P; 479666-44-9P; 479666-45-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 479666-49-4P; 479666-50-7P; 479666-51-8P; 479666-52-9P; 479666-53-0P; 479666-54-1P; 479666-55-2P; 479666-56-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 129975-11-7 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with aldehyde and isocyanoacetamide; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 124-02-7 (Diallyl amine); 136142-48-8; 479666-47-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with aldehyde and isonitrile; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 479666-38-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with allylamine and aldehyde; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 111-71-7 (Heptanal) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with allylamine and isocyanoacetamide; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 1440-28-4; 479666-48-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with amine and aldehyde; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes); 104-53-0 (Benzenepropanal); 6688-11-5 (Cyclooctanecarboxaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with amine and isonitrile; prepn. of diastereoisomeric oxa-bridged polyheterocycles and their fragmentation to corresponding pyrrolopyridines via combined multicomponent reaction/domino processes)
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