Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure
2002
Abstract
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)]
Details
Title
Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure
Author(s)
Gamez-Montano, Rocio ; Gonzalez-Zamora, Eduardo ; Potier, Pierre ; Zhu, Jieping
Published in
Tetrahedron
Volume
58
Issue
32
Pages
6351-6358
Date
2002
ISSN
0040-4020
Keywords
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)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25