A novel sugar based intramolecular Ugi 3CC for the N-alkyl-3-oxo-4-aryl-octahydrofuro[2,3-f][1,4]oxazepine-5-carboxam i des

A novel sugar based intramolecular Ugi 3CC for the N-alkyl-3-oxo-4-aryl-octahydrofuro[2,3-f][1,4]oxazepine-5-carboxam i des

An intramolecular Ugi reaction of 3-carboxy tethered sugar aldehyde with aryl amines and isocyanides has been accomplished to produce a novel class of carbohydrate derivatives, 3-oxo-4-aryl-octahydrofuro[2,3-f][1,4]oxazepine-5-carboxamides in good yields. The stereochemistry of the products was assi...

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Veröffentlicht in:Tetrahedron letters 2012-05, Vol.53 (18), p.2273-2276
Hauptverfasser: Reddy, BVSubba, Majumder, Nilanjan, Prabhakar Rao, T, Sridhar, B
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Amines
Aromatic compounds
Carbohydrates
Derivatives
Stereochemistry
Sugars
Tetrahedrons
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Zusammenfassung:An intramolecular Ugi reaction of 3-carboxy tethered sugar aldehyde with aryl amines and isocyanides has been accomplished to produce a novel class of carbohydrate derivatives, 3-oxo-4-aryl-octahydrofuro[2,3-f][1,4]oxazepine-5-carboxamides in good yields. The stereochemistry of the products was assigned by NMR studies. This is the first report on intramolecular Ugi reaction of 3-carboxy tethered sugar aldehyde, aryl amine, and isonitrile.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2012.02.048