| Summary: | In this study, we describe the synthesis of cyclic <i>N</i>-acyl amidines from readily available <i>N</i>-heteroarenes. The synthetic methodology utilized the versatile <i>N</i>-silyl enamine intermediates from the hydrosilylation of <i>N</i>-heteroarenes for the [3 + 2] cycloaddition reaction step. We evaluated various acyl azides and selected an electronically activated acyl azide, thereby achieving a reasonable yield of cyclic <i>N</i>-acyl amidines. We analyzed the relationship between the reactivity of each step and the electronic nature of substrates using in situ nuclear magnetic resonance spectroscopy. In addition, we demonstrated gram-scale synthesis using the proposed methodology.
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