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Three-Component Functionalized Dihydropyridine Synthesis via a Formal Inverse Electron-Demand Hetero-Diels–Alder Reaction

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journal contribution
posted on 17.07.2015, 00:00 by Xiaonan Yan, Fei Ling, Yuchen Zhang, Cheng Ma
A mild three-component synthetic approach to versatile 2-amino-1,4-dihydropyridines from terminal alkynes, sulfonyl azides, and N-sulfonyl-1-aza-1,3-butadienes was successfully developed and relied on the in situ generation of metalated ynamide intermediates Ib to achieve a formal inverse electron-demand hetero-Diels–Alder reaction. Experimental results suggest that alkali metal cations (Li+ and Cs+ ions) might play a critical role to achieve the cycloaddition process.

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