Palladium‐Catalyzed Domino Reaction for the Synthesis of 3‐Amino 1,2,4‐Benzothiadiazine 1,1‐Dioxides
Abstract
A palladium‐catalyzed domino reaction of 2‐azidosulfonamides and isocyanides enables the synthesis of 3‐amino‐substituted 1,2,4‐benzothiadiazine 1,1‐dioxides at room temperature. By applying commercially available Pd(dba)2 in catalyst loadings as low as 1.0 mol%, a variety of 21 differently substituted 2H‐1,2,4‐benzothiadiazine 1,1‐dioxides can be prepared within 2 h. Moreover, the developed protocol gives access to the related 4H heterocycles.
Main Authors
Format
Articles
Research article
Published
2024
Series
Subjects
Publication in research information system
Publisher
Wiley-VCH Verlag
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-202311167961Use this for linking
Review status
Peer reviewed
ISSN
1615-4150
DOI
https://doi.org/10.1002/adsc.202300875
Language
English
Published in
Advanced Synthesis and Catalysis
Citation
- Hommelsheim, R., van Nahl, R., Hanek, L. M., Ward, J. S., Rissanen, K., & Bolm, C. (2024). Palladium‐Catalyzed Domino Reaction for the Synthesis of 3‐Amino 1,2,4‐Benzothiadiazine 1,1‐Dioxides. Advanced Synthesis and Catalysis, 366(4), 717-724. https://doi.org/10.1002/adsc.202300875
License
Additional information about funding
Fondsder Chemischen Industriee.V. (Kekulé scholarship) and Friedrich-Ebert-Stiftung (Promotionsförderung) are acknowledged for supporting the doctoral studies of RH. The authors thank Benjamin James Statham (RWTH Aachen University) for critical proof reading and fruitful discussion. We thank Mrs. Susanne Pohlman for her support with the synthesis of starting materials, Marcus Frings for the measurement and analysis of HPLC samples, and Dr. Wolfgang Bettray for MS analyses and helpful discussion (all three RWTH Aachen University). In addition, we acknowledge the Alexander von Humboldt Foundation for support of K. R. (AvH research award).
Copyright© 2023 the Authors