Dual Role of C,N-Cyclic Azomethine Imine as a Dipole and an Oxidant in the Synthesis of Pyrazolidine-Fused Tetrahydroquinolines and C3-Functionalized Quinolines

초록

A selective synthesis of pyrazolidine-fused tetrahydroquinoline and C3-functionalized quinoline from N-silyl enamine and C,N-cyclic azomethine imine is presented, using [3 + 2] cycloaddition with varying reagent ratios. In this study, the C,N-cyclic azomethine imine serves dual roles as both dipole and oxidant, with the latter being unprecedented. The dual role of C,N-cyclic azomethine imine was confirmed through stepwise control reactions and deuterium-labeling studies.

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