Visible-Light-Induced [4 + 3]-Annulation of Carbonyl Ylides with Alkenyl Pyrazolinone for Constructing [4.2.1]-Oxo-Bridged Oxocine Skeleton

Dong-Sheng Ji; Xin Zhang; Peiqin Zhang; Xiazhen Bao; Yong Yuan; Congde Huo; Peng-Fei Xu

doi:10.1021/acs.orglett.4c04715

Visible-Light-Induced [4 + 3]-Annulation of Carbonyl Ylides with Alkenyl Pyrazolinone for Constructing [4.2.1]-Oxo-Bridged Oxocine Skeleton

Org Lett. 2025 Jan 6. doi: 10.1021/acs.orglett.4c04715. Online ahead of print.

Authors

Dong-Sheng Ji¹, Xin Zhang¹, Peiqin Zhang¹, Xiazhen Bao¹, Yong Yuan¹, Congde Huo¹, Peng-Fei Xu²

Affiliations

¹ College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. China.
² State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.

PMID: 39763148
DOI: 10.1021/acs.orglett.4c04715

Abstract

Herein, we present a visible-light-induced protocol for the synthesis of highly functionalized oxo-bridged oxocine skeletons. This method generates carbenes via visible-light-induced ortho-acyl diazo compounds, which are rapidly intercepted by the oxygen atom of an intermolecular acyl group to form a cyclic 1,3-dipole. The in situ generated highly reactive 1,3-dipole undergoes a facile formal [4 + 3] cycloaddition with alkenyl pyrazolinone, yielding [4.2.1]-oxo-bridged oxocine compounds.