N -Chlorosulfonyl carbamate-enabled, photoinduced amidation of quinoxalin-2(1 H )-ones.

Autor: Yuan CP; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Xie ZZ; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Zheng Y; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., He JT; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Guan JP; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Chen HB; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.; Jiangxi Time Chemical Company, Ltd., Fuzhou 344800, P. R. China., Xiang HY; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Chen K; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China., Yang H; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2023 Aug 17; Vol. 59 (67), pp. 10125-10128. Date of Electronic Publication: 2023 Aug 17.
DOI: 10.1039/d3cc02744a
Abstrakt: Reported herein is the design and development of a new photo-induced amidation protocol with the readily available N -chlorosulfonyl carbamate as an effective amidyl-radical precursor, which could be readily prepared from commercial low-cost chlorosulfonyl isocyanate (CSI) and alcohol feedstocks. The synthetic potency of this developed protocol was well demonstrated by direct amidation of various quinoxalin-2(1 H )-ones. The protocol could be further streamlined by implementing a one-pot/two-step/three-component process of CSI, alcohol, and quinoxalin-2(1 H )-one, with significantly improved reaction efficiency. This methodology offers an intriguing opportunity for rapid expansion of nitrogen-containing molecular complexity, thus inspiring comprehensive exploration of a new reaction mode of CSI reagent.
Databáze: MEDLINE