1,2,6-Thiadiazine 1-Oxides : Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides
Abstract
Unprecedented three-dimensional 1,2,6-thiadiazine 1-oxides have been prepared by an aza-Michael-addition/cyclization/condensation reaction sequence starting from sulfonimidamides and propargyl ketones. The products have been further functionalized by standard cross-coupling reactions, selective bromination of the heterocyclic ring, and conversion into a β-hydroxy substituted derivative. A representative product was characterized by single-crystal X-ray structure analysis.
Main Authors
Format
Articles
Research article
Published
2020
Series
Subjects
Publication in research information system
Publisher
American Chemical Society
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-202005043038Käytä tätä linkitykseen.
Review status
Peer reviewed
ISSN
1523-7060
DOI
https://doi.org/10.1021/acs.orglett.0c00666
Language
English
Published in
Organic Letters
Citation
- Schöbel, J.-H., Passia, M. T., Wolter, N. A., Puttreddy, R., Rissanen, K., & Bolm, C. (2020). 1,2,6-Thiadiazine 1-Oxides : Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides. Organic Letters, 12(7), 2702-2706. https://doi.org/10.1021/acs.orglett.0c00666
License
Funder(s)
Research Council of Finland
Funding program(s)
Postdoctoral Researcher, AoF
Tutkijatohtori, SA
Additional information about funding
We thank the Alexander von Humboldt Foundation for support of K.R. (AvH research award), and we gratefully acknowledge Marcus Frings (RWTH Aachen University) for measuring the HPLC data. Further thanks go to Daniela Lutsch (RWTH Aachen University) for supporting practical experiments. Financial support from the Academy of Finland (RP Grant No. 298817) is also gratefully acknowledged.
Copyright© 2020 American Chemical Society