Base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction: efficient access to δ-carboline derivatives. Issue 35 (24th August 2022)

• Record Type: Journal Article
• Authors: Sun, Xi-Shang; Diao, Xin-Yu; Dong, Xiu-Qin; Wang, Chun-Jiang
• Is Part Of: Chemical science. Volume 13:Issue 35(2022)
• Page Start: 10448
• Page End: 10454
• Publication Date: 2022-08-24
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc03166c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A serendipitous and efficient approach to access various δ-carbolines was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction in good to high yields with excellent regio/chemoselectivity. Abstract : A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of N -2, 2, 2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate tolerance. Importantly, the potential application of these fascinating δ-carboline derivative products is well demonstrated in the recognition of ferric ions.