ChemInform Abstract: Transformation of Oximes of Phenethyl Ketone Derivatives to Quinolines and Azaspirotrienones Catalyzed by Tetrabutylammonium Perrhenate and Trifluoromethanesulfonic Acid.

✍ Scribed by H. KUSAMA; Y. YAMASHITA; K. UCHIYAMA; K. NARASAKA

• Book ID: 101854619
• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199735161

✦ Synopsis

Transformation of Oximes of Phenethyl Ketone Derivatives to Quinolines and Azaspirotrienones Catalyzed by Tetrabutylammonium Perrhenate and Trifluoromethanesulfonic Acid.

-Treatment of phenethyl ketone oximes with chloranil and TfOH in the presence of catalytic amounts of Bu4NReO4 provides quinolines (cf. (II) , (III), (V)). p-Hydroxyphenalkyl ketone oximes furnish azaspirotrienones (VII) under similar conditions. Thus obtained azaspirotrienones are converted to quinolines by acid treatment. -(KUSAMA, H.; YAMASHITA, Y.; UCHIYAMA, K.;