One-pot synthesis of symmetrical bis-sulfonyl 2,6-diarylpyridines via BiCl3-catalyzed and K2S2O8-mediated domino annulation of β-ketosulfones and N, N-dimethylacetamide

Meng-Yang Chang; Chun-Yi Lin

doi:10.1039/d4ob01681e

One-pot synthesis of symmetrical bis-sulfonyl 2,6-diarylpyridines via BiCl₃-catalyzed and K₂S₂O₈-mediated domino annulation of β-ketosulfones and N, N-dimethylacetamide

Org Biomol Chem. 2024 Dec 3. doi: 10.1039/d4ob01681e. Online ahead of print.

Authors

Meng-Yang Chang^{1

2

3}, Chun-Yi Lin¹

Affiliations

¹ Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan. mychang@kmu.edu.tw.
² Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
³ NPUST College of Professional Studies, National Pingtung University of Science and Technology, Pingtung 912, Taiwan.

PMID: 39625690
DOI: 10.1039/d4ob01681e

Abstract

In this study, BiCl₃-promoted and K₂S₂O₈-mediated synthesis of diverse bis-sulfonyl 2,6-diarypyridines was developed via one-pot stepwise (2C + 2C + 1C + 1N) annulation of two molecules of β-ketosulfone and N,N-dimethylacetamide (DMAC). In the entire process, DMAC acts as the synthon of one carbon and one nitrogen in the construction of the pyridine skeleton via cascade formation of single (C-C/C-N) and double (CC/CN) bonds under refluxing DMAC conditions.