ol0c01935_si_001.pdf (16.37 MB)
Download fileUnusual Reactivity of 4‑Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate
journal contribution
posted on 09.07.2020, 21:45 authored by Pravin Kumar, Manmohan KapurAn
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.