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Unusual Reactivity of 4‑Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate

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journal contribution
posted on 09.07.2020, 21:45 by Pravin Kumar, Manmohan Kapur
An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C–C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.