Tetrahedron Letters

Synthesis of 2, 3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radical cation induced conditions

X Jia, F Peng, C Qing, C Huo, Y Wang, X Wang

Index: Jia, Xiaodong; Peng, Fangfang; Qing, Chang; Huo, Congde; Wang, Yaxin; Wang, Xicun Tetrahedron Letters, 2013 , vol. 54, # 36 p. 4950 - 4952

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Citation Number: 9

Abstract

Abstract A tandem cyclization/aromatization of anilines and aldehydes was achieved under catalytic radical cation salt induced conditions, producing a series of 2, 3-disubstituted quinolines in good yields. In this reaction, the in situ generated imine tautomerizes to enamine, which acts as a dienophile to participate in the tandem cyclization, and further elimination of the anilino group triggers the aromatization of tetrahydroquinolines, ...