Liquid-phase synthesis of polyhydroquinoline using task-specific ionic liquid technology.
A new strategy for the synthesis of polyhydroquinolines from task-specific ionic liquids (TSIL) as a soluble support was developed. The preparation of the polyhydroquinolines by a three-component reaction was achieved by using ionic liquid-phase bound beta-oxo esters. These starting functionalized esters were synthesized by a solventless transesterification without catalyst under microwave irradiation. The structure of the intermediates in each step was verified routinely by spectroscopic analysis, and after oxidation of the polyhydroquinolines grafted on the TSIL with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or after cleavage (transesterification, saponification-acidification), the target compounds were obtained in good yields and high purities.
Legeay
Jean Christophe
JC
Laboratoire Sciences Chimiques de Rennes, Université de Rennes 1, UMR CNRS 6226, Groupe Ingénierie Chimique & Molécules pour le Vivant (ICMV), Bât. 10A, Campus de Beaulieu, Avenue du Général Leclerc, CS 74205, 35042 Rennes Cedex, France.
Goujon
Jean Yves
JY
Vanden Eynde
Jean Jacques
JJ
Toupet
Loic
L
Bazureau
Jean Pierre
JP
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008872:Microwaves; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012680:Sensitivity and Specificity
D004952:Esters; D011108:Polymers; D011804:Quinolines