Synthesis of 1,2-Benzothiazines by a Rhodium-Catalyzed Domino C–H Activation/Cyclization/Elimination Process from S‑Aryl Sulfoximines and Pyridotriazoles

A method for the synthesis of a large number of 1,2-benzothiazines bearing pyridyl as well as carbonyl groups is developed from rhodium-catalyzed carbene insertions into aromatic C–H bonds of S-aryl sulfoximines using pyridotriazoles by denitrogenative cyclization followed by the elimination of alco...

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Veröffentlicht in:Organic letters 2016-07, Vol.18 (14), p.3498-3501
Hauptverfasser: Jeon, Woo Hyung, Son, Jeong-Yu, Kim, Ji Eun, Lee, Phil Ho
Format: Artikel
Sprache:eng
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Zusammenfassung:A method for the synthesis of a large number of 1,2-benzothiazines bearing pyridyl as well as carbonyl groups is developed from rhodium-catalyzed carbene insertions into aromatic C–H bonds of S-aryl sulfoximines using pyridotriazoles by denitrogenative cyclization followed by the elimination of alcohols. The present method involves the N–H/C–H activation of simple alkyl aryl sulfoximines and has the advantages of a broad substrate scope, high functional group tolerance, and good regioselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01750