Selective 6π-Electrocyclization of N-Vinyl-α,β-Unsaturated Nitrones to Prepare Polysubstituted Pyridine Derivatives
Li-Yao Ding , Yan-Jiao Lu , Jin-Hong Pang , Hai-Fang Lin , Chun-Hua Chen , Hong-Yan Bi , Dong-Liang Mo
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (11) : 1287 -1292.
Selective 6π-Electrocyclization of N-Vinyl-α,β-Unsaturated Nitrones to Prepare Polysubstituted Pyridine Derivatives
Herein, we have developed a facile method for the synthesis of various polysubstituted pyridine derivatives through selective 6π-electrocyclization of N-vinyl-α,β-unsaturated nitrones. It was found that gold catalysts promoted carbon-6π-electrocyclization of N-vinyl-α,β-unsaturated nitrones to afford 6-alkenyl pyridine N-oxides in 43%—75% yields, whereas copper catalysts facilitated oxygen-6π-electrocyclization to give 6-epoxy pyridines in 41%—83% yields. The present method features broad substrate scope, good functional group tolerance, high cyclization selectivity, and diversity of polysubstituted pyridine scaffolds.
Nitrones / 6π-Electrocyclization / Gold catalysis / Copper catalysis / Pyridine / Nitrogen heterocycles / Epoxidation / Cyclization
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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