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. 2023 Mar 1;29(13):e202203729.
doi: 10.1002/chem.202203729. Epub 2023 Jan 23.

A Copper-Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine-1-oxides

Renè Hommelsheim  1 , Sandra Bausch  1 , Arjuna Selvakumar  1 , Mostafa M Amer  1   2 , Khai-Nghi Truong  3 , Kari Rissanen  3 , Carsten Bolm  1
Affiliations

A Copper-Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine-1-oxides

Renè Hommelsheim et al. Chemistry. .

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.

Keywords: CLICK; copper catalysis; cycloaddition; domino reactions; sulfoximines; sulfur heterocycles.

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References

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