A rhodium-catalyzed route for oxidative coupling and cyclization of 2-aminobenzyl alcohol with ketones leading to quinolines

✍ Scribed by Chan Sik Cho; Hyo Jin Seok; Sang Oral Shim

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2005
• Tongue: English
• Weight: 100 KB
• Volume: 42
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570420630

✦ Synopsis

Aminobenzyl alcohol undergoes oxidative cyclization with aryl(alkyl), alkyl(alkyl) and cyclic ketones in dioxane at 80°in the presence of a catalytic amount of RhCl(PPh 3 ) 3 along with KOH to afford the corresponding quinolines in good yields. The catalytic pathway seems to be proceeded via a sequence involving initial oxidation of 2-aminobenzyl alcohol to 2-aminobenzaldehyde by a rhodium catalyst, cross aldol reaction between 2-aminobenzaldehyde and ketones, and cyclodehydration.