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

Hommelsheim, Renè; Bausch, Sandra; Selvakumar, Arjuna; Amer, Mostafa M.; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten

doi:10.1002/chem.202203729

dc.contributor.author	Hommelsheim, Renè
dc.contributor.author	Bausch, Sandra
dc.contributor.author	Selvakumar, Arjuna
dc.contributor.author	Amer, Mostafa M.
dc.contributor.author	Truong, Khai-Nghi
dc.contributor.author	Rissanen, Kari
dc.contributor.author	Bolm, Carsten
dc.date.accessioned	2023-03-14T07:18:38Z
dc.date.available	2023-03-14T07:18:38Z
dc.date.issued	2023
dc.identifier.citation	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. <i>Chemistry: A European Journal</i>, <i>29</i>(13), Article e202203729. <a href="https://doi.org/10.1002/chem.202203729" target="_blank">https://doi.org/10.1002/chem.202203729</a>
dc.identifier.other	CONVID_164441954
dc.identifier.uri	https://jyx.jyu.fi/handle/123456789/85999
dc.description.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.	en
dc.format.mimetype	application/pdf
dc.language.iso	eng
dc.publisher	Wiley-VCH Verlag
dc.relation.ispartofseries	Chemistry: A European Journal
dc.rights	CC BY 4.0
dc.title	A Copper‐Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine‐1‐oxides
dc.type	research article
dc.identifier.urn	URN:NBN:fi:jyu-202303142153
dc.contributor.laitos	Kemian laitos	fi
dc.contributor.laitos	Department of Chemistry	en
dc.contributor.oppiaine	Orgaaninen kemia	fi
dc.contributor.oppiaine	Organic Chemistry	en
dc.type.uri	http://purl.org/eprint/type/JournalArticle
dc.type.coar	http://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatus	peerReviewed
dc.relation.issn	0947-6539
dc.relation.numberinseries	13
dc.relation.volume	29
dc.type.version	publishedVersion
dc.rights.copyright	© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH
dc.rights.accesslevel	openAccess	fi
dc.type.publication	article
dc.subject.yso	katalyysi
dc.subject.yso	kemiallinen synteesi
dc.subject.yso	heterosykliset yhdisteet
dc.subject.yso	kupari
dc.format.content	fulltext
jyx.subject.uri	http://www.yso.fi/onto/yso/p8704
jyx.subject.uri	http://www.yso.fi/onto/yso/p8468
jyx.subject.uri	http://www.yso.fi/onto/yso/p38837
jyx.subject.uri	http://www.yso.fi/onto/yso/p19074
dc.rights.url	https://creativecommons.org/licenses/by/4.0/
dc.relation.doi	10.1002/chem.202203729
jyx.fundinginformation	R.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.
dc.type.okm	A1

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

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