Naslov
Efficient synthesis of chiral amides of 2-(2 '-carboxyphenyl)-4-hydroxy-quinoline
(Efficient Synthesis of Chiral Amides of 2-(2´-Carboxyphenyl)-4-hydroxyquinoline)

Autori
Hameršak, Zdenko ; Litvić, Mladen ; Šepac, Dragan ; Lesac, Andreja ; Raza, Zlatica ; Šunjić, Vitomir

Izvornik
Synthesis-Stuttgart (0039-7881) 15 (2002); 2174-2176

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Quinolines ; Amides ; Stereoselective synthesis ; Alkylations ; Heterocycles

Sažetak
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).

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA