A Novel Multicomponent Synthesis of Polysubstituted 5-Aminooxazole and Its New Scaffold-Generating Reaction to Pyrrolo[3,4-b]pyridine

A novel three-component synthesis of 5-aminooxazoles is reported. Its subsequent reaction with alpha ,beta -unsatd. acyl chloride leads to polysubstituted pyrrolopyridines. A triple domino process, acylation/IMDA/retro-Michael cycloreversion, was involved in the latter process. The methodol. allows the quick prepn., from simple and readily available inputs, of highly functionalized title compds. not easily accessed by other methods. [on SciFinder (R)]


Published in:
Organic Letters, 3, 6, 877-880
Year:
2001
Keywords:
Note:
CAN 134:326420
28-2
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
written in English.
100-81-2 (3-Methylbenzylamine); 110-91-8 (Morpholine); 111-71-7 (Heptanal); 120-20-7 (3,4-Dimethoxyphenethylamine); 123-72-8 (Butanal); 140-75-0 (4-Fluorobenzylamine); 2393-23-9 (4-Methoxybenzylamine); 2577-48-2; 2780-89-4 (Methyl 6-aminohexanoate); 6688-11-5 (Formylcyclooctane); 22440-58-0; 34446-64-5; 34967-24-3 (3,5-Dimethoxybenzylamine); 66130-92-5; 85059-48-9; 336105-88-5 Role: RCT (Reactant), RACT (Reactant or reagent) (multicomponent synthesis of polysubstituted aminooxazoles and prepn. of pyrrolopyridines); 336105-90-9P; 336105-92-1P; 336105-94-3P; 336105-95-4P; 336105-96-5P; 336105-97-6P; 336105-98-7P; 336105-99-8P; 336106-17-3P; 336106-18-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (multicomponent synthesis of polysubstituted aminooxazoles and prepn. of pyrrolopyridines); 336106-00-4P; 336106-02-6P; 336106-05-9P; 336106-07-1P; 336106-09-3P; 336106-11-7P; 336106-13-9P; 336106-15-1P Role: SPN (Synthetic preparation), PREP (Preparation) (multicomponent synthesis of polysubstituted aminooxazoles and prepn. of pyrrolopyridines)
Laboratories:




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


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