A Copper‐Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine‐1‐oxides
Hommelsheim, R., Bausch, S., Selvakumar, A., Amer, M. M., Truong, K.-N., Rissanen, K., & Bolm, C. (2023). A Copper‐Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine‐1‐oxides. Chemistry: A European Journal, 29(13), Article e202203729. https://doi.org/10.1002/chem.202203729
Published inChemistry: A European Journal
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH
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.
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Additional information about fundingR.H. gratefully acknowledges support by the Fonds der Chemischen Industrie e.V. (Kekulé scholarship) and by the Friedrich-Ebert-Stiftung (Promotionsförderung). M. M. Amer thanks the Leibniz-Gemeinschaft for financial support (project PHARMSA K136/2018), and we acknowledge the Alexander von Humboldt Foundation for support of K.R. (AvH research award). The authors thank Mrs. Susanne Pohlmann for her support in synthetic work, Christian Schumacher for his help in the preparation of X-ray samples and fruitful discussion, Victoria Pfennig for critical proofreading, and Dr. Christoph Räuber (all RWTH Aachen University) for mechanistic NMR studies. ...
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