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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.


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

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PMID: 22316241

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