Cyclic Bifunctional Reagents Enabling a Strain-Release-Driven Formal [3 + 2] Cycloaddition of 2H-Azirines by Cascade Energy Transfer

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

The energy transfer (EnT)-catalyzed ring opening and further decarboxylation of isoxazole-5(4H)-ones enables the in situ generation strained 2H-azirines. Subsequent selective C(sp2)-C(sp3) bond cleavage azirine intermediate allows a formal [3 + 2] cycloaddition with wide range electrophiles, unlocking access to valuable pyrroline-type moieties. Mechanistic experiments combination density functional theory (DFT) calculations revealed unique nature EnT-cascade process for three-membered aza-cycle while providing insight into regio- diastereoselectivity annulation. This mild straightforward method ensures rapid construction highly substituted cyclic imines, which can be easily converted pyrrolidines, fused oxaziridines, biologically relevant β-amino acid precursors.

Language: Английский

---

Light-induced synthesis of 2H-azirines and its applications in organic chemistry

Journal of Saudi Chemical Society, Journal Year: 2024, Volume and Issue: 28(2), P. 101831 - 101831

Published: March 1, 2024

2H-azirines have represented versatile building motifs in the domain of organic chemistry owing to their excellent reaction activity induced by high strain three-membered ring species. Over past decades, brilliant achievements been made 2H-azirine involving construction as well transformation such functional compounds. In presence transition metals, strong bases or oxidants, could be converted into corresponding products under harsh conditions. Different from traditional catalytic methods, utilization photochemistry has proved an extremely fascinating protocol that facilitates blocks diverse substrates and further conversion various derivatives with interesting biological activities. this regard, more light-driven synthetic approaches featuring efficiency mild conditions developed. Herein, we summarized accessibility applications powerful precursors key intermediates for synthesis biologically promising molecules photocatalytic

Language: Английский

---

Visible light-promoted synthesis of 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dionesvia[3+2] cycloaddition reaction of 2H-azirines with maleimides

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(12), P. 5634 - 5638

Published: Jan. 1, 2023

Diastereoselective synthesis of pyrrolo[3,4- c ]pyrrole-1,3-dione derivitives from 2 H -azirines and N -substituted maleimides through an efficient environmentally friendly visible light-induced cycloaddition reaction.

Language: Английский

---

Organophotoredox‐mediated Formal [3+2]‐Cycloaddition of 2H‐Azirines with Aryldiazonium Salts: Direct Access to Trisubstituted 1,2,4‐Triazoles

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(7)

Published: Feb. 28, 2023

The present work documents an organophotoredox-mediated formal [3+2]-cycloaddition of 2H-azirines with aryl diazonium tetrafluoroborate salts to furnish 1,3,5-trisubstituted 1,2,4-triazoles. reaction furnishes a regioisomeric mixture 1,2,4-triazoles in case unsymmetrically substituted azirines. It is noteworthy that radical generation from salt under visible light photoredox conditions could be successfully avoided by carefully selecting the conditions.

Language: Английский

---