Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones from 2-formylbenzoic acid

Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones from 2-formylbenzoic acid

Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones is reported. The synthetic method involves the preparation of dimethyl isoindolin-1-one-3-yl-phosphonates by a ‘one-pot’ three-component reaction of 2-formylbenzoic acid with 4-methoxybenzylamine or aminoacetaldehyde...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 53; no. 43; pp. 5756 - 5758
Main Authors: Reyes-Gonzalez, Miguel Angel, Zamudio-Medina, Angel, Ordonez, Mario
Format: Journal Article
Language:English
Published: Elsevier Ltd 24-10-2012
Subjects:
2-Formylbenzoic acid
3-Methyleneisoindolin-1-ones
Aldehydes
Aminophosphonates
Aromatic compounds
Dimethyl
Dimethyl acetals
Horner reaction
Inorganic salts
One-pot three-component reaction
Solvents
Synthesis (chemistry)
Tetrahedrons
One-pot three-component reaction
Aminophosphonates
2-Formylbenzoic acid
Horner reaction
3-Methyleneisoindolin-1-ones
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Summary:Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones is reported. The synthetic method involves the preparation of dimethyl isoindolin-1-one-3-yl-phosphonates by a ‘one-pot’ three-component reaction of 2-formylbenzoic acid with 4-methoxybenzylamine or aminoacetaldehyde dimethyl acetal and dimethyl phosphite under solvent and catalyst free-conditions, followed by a Horner reaction with several aryl aldehydes.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.08.040