Synthesis of polysubstituted, functionalized quinolines through a metal-free domino process involving a C4–C3 functional group rearrangement.
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.
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Plaza de Ramón y Cajal, s.n., 28040 Madrid, Spain.
Pascual
P
Ribelles
M Teresa
MT
Ramos
J Carlos
JC
Menéndez
D002384:Catalysis; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D011804:Quinolines; C542964:1,2,3,4-tetrahydroquinoline