Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure

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)]


Published in:
Tetrahedron, 58, 32, 6351-6358
Year:
2002
Keywords:
Note:
CAN 138:73220
28-15
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
0040-4020
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:




 Record created 2010-11-25, last modified 2018-03-17


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