A Copper‐Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine‐1‐oxides. Issue 13 (23rd January 2023)

• Record Type: Journal Article
• Authors: Hommelsheim, Renè; Bausch, Sandra; Selvakumar, Arjuna; Amer, Mostafa M.; Truong , Khai‐Nghi; Rissanen, Kari; Bolm, Carsten
• Is Part Of: Chemistry. Volume 29:Issue 13(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-01-23
• Subjects: CLICK -- copper catalysis -- cycloaddition -- domino reactions -- sulfoximines -- sulfur heterocycles; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202203729
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Copper(I)‐catalyzed domino reactions of 2‐azido sulfoximines with 1‐iodoalkynes yield fused triazolyl‐containing benzothiadiazine‐1‐oxides. The protocol features the synthesis of two fused heterocyclic rings in one step with good to excellent yields and a broad functional group tolerance. Detailed mechanistic investigations indicate that a copper π‐complex initiates a cycloaddition and oxidative C−N coupling reaction sequence. The results suggest an interrupted domino process involving an iodinated triazole as a key intermediate. Abstract : A copper(I)‐catalyzed interrupted domino reaction of 2‐azido sulfoximines with 1‐iodoalkynes affords fused triazolyl‐containing benzothiadiazine‐1‐oxides in good to excellent yields. The substrate scope is broad and the functional group tolerance high. Mechanistic studies suggest a reaction pathway via copper π‐complexes and a consecutive oxidative coupling of a relevant iodinated triazole as intermediate.