Sequential amino-Claisen rearrangement/intramolecular 1,3-dipolar cycloaddition/reductive cleavage approach to the stereoselective synthesis of cis-4-hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1H)-benzazepines

Abstract:

A novel stereoselective synthesis of cis-2-aryl-4-hydroxy-2,3,4,5- tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involves N-allylation of corresponding N-benzylanilines followed by amino-Claisen rearrangement, subsequent oxidation with in situ 1,3-dipolar cycloaddition affording isoxazolidines, and finally reductive cleavage of the isoxazolidinic N-O bond. © Georg Thieme Verlag Stuttgart.

Año de publicación:

2006

Keywords:

• Intramolecular 1,3-dipolar cycloaddition
• Ortho-allylanilines
• Reductive cleavage
• Tetrahydro-1-benzazepines
• Amino-Claisen rearrangement

Fuente:

scopus