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, Jan-Hendrik; Elbers, Philipp; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten (2021). 1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions. Advanced Synthesis and Catalysis, Early online. DOI: 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: Early online

Publisher: Wiley-VCH Verlag

Publication country: Germany

Publication language: English

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

Open Access: Publication channel is not openly available

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

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: No, publication in press

Preliminary JUFO rating: 2