ChemInform Abstract: The Palladium-Catalyzed Transfer Hydrogenation/Heterocyclization of β-(2-Aminophenyl)-α,β-ynones. An Approach to 2-Aryl- and 2-Vinylquinolines.

✍ Scribed by Sandro Cacchi; Giancarlo Fabrizi; Fabio Marinelli

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199931179

✦ Synopsis

The Palladium-Catalyzed Transfer Hydrogenation/Heterocyclization of β-(2-Aminophenyl)-α,β-ynones.

An Approach to 2-Aryl-and 2-Vinylquinolines.

-Readily available β-(o-aminophenyl)-α,β-ynones undergo efficient Pd-catalyzed transfer hydrogenation according to A) or B) providing α-substituted quinolines directly as major or sole products. The attempt to prepare diarylquinolines leads to a mixture of regioisomers [cf. (XIV and (XV)]. The N-acylated substrate (XVI) forms a benzoxazine instead of the expected quinoline.