A1 Journal article (refereed)
1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions (2021)


Schöbel, J.-H., Elbers, P., Truong, K.-N., Rissanen, K., & Bolm, C. (2021). 1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions. Advanced Synthesis and Catalysis, 363(5), 1322-1329. https://doi.org/10.1002/adsc.202001505


JYU authors or editors


Publication details

All authors or editors: Schöbel, Jan-Hendrik; Elbers, Philipp; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten

Journal or series: Advanced Synthesis and Catalysis

ISSN: 1615-4150

eISSN: 1615-4169

Publication year: 2021

Volume: 363

Issue number: 5

Pages range: 1322-1329

Publisher: Wiley-VCH Verlag

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/adsc.202001505

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/74041

Additional information: This article also appears in: Hot Topic: C-H Activation


Abstract

Three‐dimensional aza‐analogues of 1,2‐benzothiazine 1,1‐dioxides have been prepared from sulfonimidamides. Two different protocols are presented. The first is a rhodium‐catalyzed annulation reaction with alpha‐sulfonyloxyketones leading to 4 unsubstituted benzothiazine derivatives. By selective bromination with NBS the heterocyclic ring can further be functionalized. In the second approach, an iridium catalyst is applied under solvent‐free mechanochemical conditions providing products with 3,4‐disubstituted thiazine rings from diazoketo esters and diazoketo sulfones.


Keywords: organic compounds; sulphur compounds; chemical synthesis; catalysis

Free keywords: 1,2-benzothiazine; C−H activation; mechanochemistry; iridium catalysis; rhodium catalysis; sulfonimidamide


Contributing organizations


Ministry reporting: Yes

Reporting Year: 2021

Preliminary JUFO rating: 2


Last updated on 2021-09-08 at 18:10