Construction of 3,6-Difluoropyridones via a Double Defluorinative [3 + 3] Annulation of α-Fluoro-α-sulfonylacetamides with 2-CF₃-Alkenes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 8, 2025

A remarkably simple and efficient double defluorinative [3 + 3] annulation approach involving N-phenyl-α-fluoro-α-phenylsulfonylacetamide 2-CF3-alkenes to access N-phenyl-3,6-difluoropyridone derivatives has been achieved. The key the success of this single-step synthesis difluoropyridones is strategic utilization for consecutive allylic vinylic substitution reactions a desulfonylation cascade. We could also show that these serve as versatile platform C-6-selective functionalizations.

Язык: Английский

Domino Michael/Oxa-Michael Reactions of the Unsymmetric Double Michael Acceptor for Access to Bicyclic Furo[2,3-b]pyrrole

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5883 - 5895

Опубликована: Апрель 10, 2024

By creating an unsymmetric double Michael acceptor 1, we were able to synthesize the nonaromatic-fused bicyclic furo[2,3-b]pyrrole nucleus using a domino Michael/oxa-Michael reaction. Adopting benzoyl acetonitrile 2d (CN as electron-withdrawing group) substrate, discovered (DHQ)2AQN-catalyzed method for high diastereo- and enantioselectivity of those products. The reaction path has been determined by isolating intermediates, density functional theory calculations support these findings. Beyond providing synthetic approach, this work illustrated compounds' possible use in antitumor activity.

Язык: Английский

Facile synthesis of dihydroisobenzofuran derivatives via a one-pot sequential Passerini-azide/Ag(I)-catalyzed cyclization process

Tetrahedron, Год журнала: 2024, Номер 158, С. 133984 - 133984

Опубликована: Апрель 13, 2024

Язык: Английский