Synthesis of polysubstituted, functionalized quinolines through a metal-free domino process involving a C4–C3 functional group rearrangement.

Pascual Ribelles, M Teresa Ramos, J Carlos Menéndez

Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Plaza de Ramón y Cajal, s.n., 28040 Madrid, Spain.

Organic letters 2012 Mar 16

filter terms:

4-Alkyl-1,2,3,4-tetrahydroquinolines bearing a 4-vinyl unit ending in an electron-withdrawing group were efficiently transformed into polysubstituted, C(3)-functionalized quinolines upon heating in refluxing o-dichlorobenzene, in a domino reaction involving an unusual C(4)-C(3) functional group rearrangement.

Citation

Pascual Ribelles, M Teresa Ramos, J Carlos Menéndez. Synthesis of polysubstituted, functionalized quinolines through a metal-free domino process involving a C4–C3 functional group rearrangement. Organic letters. 2012 Mar 16;14(6):1402-4