Synthesis of E-oxo Acids by Photostimulated Reactions of 2-(2-Iodophenyl)acetate Ion With Carbanions by the SRN1 Mechanism. Synthesis of Novel 3-Benzazepin-2-ones

MARÍA E. BUDÉN

ARKIVOC - ONLINE JOURNAL OF ORGANIC CHEMISTRY

ARKAT USA INC

Año: 2011 vol. vii p. 389 - 389

1551-7004

he synthesis of 3-benzazepin-2-ones using commercially available 2-(2-iodophenyl)acetic acid as starting material is described. The synthetic strategy involves the SRN1 substitution reaction in DMSO as solvent under photoinitiation, using ketone enolate ions as nucleophiles to obtain ε- oxo acids, followed by a condensation reaction of ε-oxo acids with ammonium acetate in glacial acetic acid to produce novel 3-benzazepin-2-ones. The target compounds are afforded in regular to good yields and the factors governing the distribution of substitution products are discussed.