Ammonium Chloride-Promoted Four-Component Synthesis of Pyrrolo[3,4-b]pyridin-5-ones

A novel multicomponent synthesis of 5-aminooxazoles starting from simple and readily available inputs is described. Thus, simply heating a methanol soln. of an aldehyde, an amine, and an alpha -isocyanoacetamide provided 5-aminooxazoles, e.g., I, in good to excellent yield. The reaction of the 5-aminooxazoles with ClCOCH:CHCOOEt led to the formation of pyrrolo[3,4-b]pyridin-5-ones, e.g., II, in a single operation. A triple domino sequence, acylation/IMDA/retro-Michael cycloreversion, is involved in this new scaffold-generating reaction. After the observation that ammonium chloride can significantly accelerate the oxazole formation in toluene, a one-pot four-component synthesis of the pyrrolo[3,4-b]pyridin-5-ones is developed. [on SciFinder (R)]

Published in:
Journal of the American Chemical Society, 124, 11, 2560-2567
CAN 136:309868
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
written in English.
142-08-5 (2-Pyridinol); 12125-02-9 (Ammonium chloride) Role: CAT (Catalyst use), USES (Uses) (ammonium chloride-promoted four-component synthesis of pyrrolo[3,4-b]pyridin-5-ones); 100-52-7 (Benzaldehyde); 100-81-2 (m-Methylbenzylamine); 104-88-1 (4-Chlorobenzaldehyde); 109-73-9 (Butylamine); 110-91-8 (Morpholine); 111-71-7 (Heptanal); 120-20-7 (3,4-Dimethoxyphenethylamine); 123-11-5 (4-Methoxybenzaldehyde); 123-72-8 (Butanal); 140-75-0 (p-Fluorobenzylamine); 1926-80-3; 2133-40-6; 2393-23-9 (p-Methoxybenzylamine); 6688-11-5 (Cyclooctanecarboxaldehyde); 7524-50-7; 13033-84-6; 32213-95-9; 34967-24-3 (3,5-Dimethoxybenzylamine); 66130-92-5; 85059-48-9; 336105-88-5; 411222-55-4 Role: RCT (Reactant), RACT (Reactant or reagent) (ammonium chloride-promoted four-component synthesis of pyrrolo[3,4-b]pyridin-5-ones); 336105-90-9P; 336105-92-1P; 336105-94-3P; 336105-95-4P; 336105-96-5P; 336105-97-6P; 336105-98-7P; 336106-00-4P; 336106-18-4P; 411222-56-5P; 411222-57-6P; 411222-58-7P; 411222-59-8P; 411222-60-1P; 411222-61-2P; 411222-76-9P; 411222-77-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (ammonium chloride-promoted four-component synthesis of pyrrolo[3,4-b]pyridin-5-ones); 336106-05-9P; 336106-07-1P; 336106-09-3P; 336106-13-9P; 336106-15-1P; 411222-62-3P; 411222-63-4P; 411222-64-5P; 411222-65-6P; 411222-66-7P; 411222-67-8P; 411222-68-9P; 411222-69-0P; 411222-70-3P; 411222-71-4P; 411222-72-5P; 411222-73-6P; 411222-74-7P; 411222-75-8P; 411222-78-1P Role: SPN (Synthetic preparation), PREP (Preparation) (ammonium chloride-promoted four-component synthesis of pyrrolo[3,4-b]pyridin-5-ones)

 Record created 2010-11-25, last modified 2018-09-13

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