Tetrahedron

A versatile synthesis of 2-substituted 4-amino-1, 2, 4, 5-tetrahydro-2-benzazepine-3-ones

K Van Rompaey, I Van den Eynde, N De Kimpe…

Index: Van Rompaey, Karolien; Van Den Eynde, Isabelle; De Kimpe, Norbert; Tourwe, Dirk Tetrahedron, 2003 , vol. 59, # 24 p. 4421 - 4432

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Citation Number: 41

Abstract

A mild and general strategy for the synthesis of 2-substituted 4-amino-1, 2, 4, 5-tetrahydro-2- benzazepine-3-ones is described. The seven-membered lactam is prepared by intramolecular amide bond formation from the intermediate amino acid, which is obtained either by reductive alkylation of a variety of amines with N-Boc, N-Me-ortho-formyl-Phe and Phth-ortho-formyl-Phe, or by reductive amination of a variety of aldehydes with N-Boc- ...