Synthesis of methylpyridine derivatives. XXXIV. Condensation of acetoacetamide with ketones to form pyridone derivatives.

Asymmetric Hydrogenation of Substituted 2-Pyrones

“…3-Hexyl-4-hydroxy-6-undecyl-2 H -pyran-2-one ( 3a ) was kindly provided by F. Hoffmann- La Roche. 4,6-Dimethyl-2 H -pyran-2-one( 3g ), 4-methoxy-6-methyl-2 H -pyran-one( 3f ), 4,6-dimethylpyridone ( 3l ), 1,4,6-trimethylpyridone ( 3m ), and 5,6-dihydro-4-hydroxy-6-methyl-2 H -pyran-2-one ( 4e ) , were prepared according to published methods. 4-Hydroxy-6-methyl-2 H -pyran-2-one ( 3e ), ethyl isodehydracetate ( 3i ), 4,6-diphenyl-2 H -pyran-2-one ( 3k ), 4,5-dihydro-5-methylene-2(3 H )-furanone ( 8 ), 4-hydroxy-3-pentenoic acid γ-lactone (α-angelicalactone) ( 9 ), 3-methyl-2-cyclohexenone ( 11 ), and 3-methyl-2-cyclopentenone ( 12 ) were purchased from Fluka, Aldrich, Acros, or Interchim S. A. and were purified by recrystallization or kugelrohr distillation prior to use.…”

Design, synthesis, and biological evaluation of tetrahydroquinolinones and tetrahydroquinolines with anticancer activity

“…We synthesized the new PI3K inhibitors through the following pathway (Scheme 1 ). In the first step, we used a modified procedure for the synthesis of tetrahydroquinolin-2(1H)-one core ( 9 ) 25 , 26 . During condensation, we found out that it is additionally necessary to remove water formed with anhydrous MgSO 4 .…”

Heterocycles with a bridgehead nitrogen atom. 16. Assembly of a peri-fused system from an angular tricycle by recyclization of an oxazole ring into pyrrole one

“…6 Compound 7 was prepared according to a known procedure. 10 2 Methoxy 4 methyl 5,6,7,8 tetrahydroquinoline (8). A mix ture of 4 methyl 5,6,7,8 tetrahydroquinolin 2 one (7) (57 mmol), CH 3 I (72 mmol), and freshly prepared and well dried Ag 2 CO 3 (28.5 mmol) in 90 mL of benzene was refluxed for 50 to 60 h in a light protected flask.…”