Efficient Synthesis of Chiral Amides of 2-(2´-Carboxyphenyl)-4-hydroxyquinoline (CROSBI ID 94471)
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Hameršak, Zdenko ; Litvić, Mladen ; Šepac, Dragan ; Lesac, Andreja ; Raza, Zlatica ; Šunjić, Vitomir
engleski
Efficient Synthesis of Chiral Amides of 2-(2´-Carboxyphenyl)-4-hydroxyquinoline
On deprotonation by lithium bistrimethylsilylamide (LBTSA), 2-phthalimidoacetophenone (1) is quantitatively converted to 6H, 12H-isoindolo [2, 1-a]-6, 7a-dihydroxyquinolin-12-one (2) ; weaker bases proved much less effective. Thermal dehydration of 2 to vinilogous imide 3, then the AlCl3-catalyzed aminolysis by (1S)-arylethylamines afforded (IS)-amides of 2-(2'-carboxyphenyl)-4-hydroxyquinolines (5-7). This sequence represents an efficient assembling of novel chiral heterocycles, potentially useful in enantioselection as ligands or chiral selectors. In situ prepared Pd(II) complexes of 5-7 exhibited catalytic activity in allylic alkylation of 1, 3-diphenyt-1-acetoxyprop-2-ene (8) by dimethylmalonate anion ; the complex of 7 afforded the highest (64%) enantiomeric excess of 1, 3-diphenyl-1-dimetylmalonylprop-2-ene (9).
Quinolines ; Amides ; Stereoselective synthesis ; Alkylations ; Heterocycles
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