Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines: a versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones.
[reaction: see text] The first successful use of ketene dithioacetals as dienophiles in the aza-Diels-Alder reaction with N-arylimines is described. Among the ketene dithioacetals tested, 1,4-benzodithiafulvenes are most effective in assembling the tetrahydroquinoline core. Subsequent chemical manipulations provide a concise and divergent approach to the synthesis of 2,3-tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones.
Cheng
Dai
D
Deltagen Research Laboratories, 4570 Executive Drive, Suite 400, San Diego, California, USA.
Zhou
Jinglan
J
Saiah
Eddine
E
Beaton
Graham
G