Gamez-Montano, RocioGonzalez-Zamora, EduardoPotier, PierreZhu, Jieping2010-11-252010-11-252010-11-25200210.1016/S0040-4020(02)00634-8https://infoscience.epfl.ch/handle/20.500.14299/58502Novel 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)]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 processtext::journal::journal article::research article