Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 21, Issue 24, Pages 5021-5032Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ob00597f
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This study reports the Lewis base dependent (3 + 3) annulation of delta-acetoxy allenoates with benzofuranone, pyrazolone, and Boc-protected oxindole. In the presence of catalytic DBU, oxindole, benzofuranone, and pyrazolone undergo (3 + 3) annulation with delta-acetoxy allenoates via 6-exo-dig cyclization at room temperature (25 degrees C) to afford fused pyran scaffolds. On the other hand, by employing catalytic DMAP, the reaction between N-Boc-oxindole and delta-acetoxy allenoates goes through 6-endo-dig cyclization, leading to distinct dihydropyrans that contain an exocyclic double bond; similar products were also obtained by using benzofuranone and pyrazolone.
Lewis base dependent (3 + 3) annulation of delta-acetoxy allenoates with benzofuranone, pyrazolone, and Boc-protected oxindole is reported. In the presence of catalytic DBU, oxindole, benzofuranone, and pyrazolone undergo (3 + 3) annulation with delta-acetoxy allenoates via 6-exo-dig cyclisation at room temperature (25 degrees C) to afford fused pyran scaffolds. On the other hand, by employing catalytic DMAP, the reaction between N-Boc-oxindole and delta-acetoxy allenoates goes through 6-endo-dig cyclisation, leading to distinct dihydropyrans that contain an exocyclic double bond; similar products were also obtained by using benzofuranone and pyrazolone.
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