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Synlett
DOI: 10.1055/a-2602-6899
letter

Synthesis of 5-Functionalized 1-(Hetero)Aryl-1,2-Thiazine 1-Oxides Through the CSIC Reaction Strategy

Yaroslav O. Chuchvera
1   Organic Synthesis, Enamine Ltd, Kyiv, Ukraine (Ringgold ID: RIN376198)
2   Chemistry Department, Kiev National Taras Shevchenko University, Kyiv, Ukraine
,
Oleksandr P. Korobka
1   Organic Synthesis, Enamine Ltd, Kyiv, Ukraine (Ringgold ID: RIN376198)
3   Chemistry Department, VN Karazin Kharkiv National University, Kharkiv, Ukraine
,
Yurii O. Horbatochkin
1   Organic Synthesis, Enamine Ltd, Kyiv, Ukraine (Ringgold ID: RIN376198)
3   Chemistry Department, VN Karazin Kharkiv National University, Kharkiv, Ukraine
,
Eugeniy Ostapchuk
4   Department of Organic Chemistry, Taras Shevchenko National University of Kyiv, Kiiv, Ukraine (Ringgold ID: RIN111229)
,
Maria Popova
5   Chemistry Department, Kiev National Taras Shevchenko University, Kiev, Ukraine
6   Department for the Synthesis of Macromolecules, Max Planck Institute for Polymer Research, Mainz, Germany (Ringgold ID: RIN28308)
,
Svetlana Shishkina
7   Department of X-ray Diffraction Studies and Quantum Chemistry, State Scientific Institution “Institute for Single Crystals” National Academy of Science of Ukraine, Kharkiv, Ukraine
,
Yulian M. Volovenko
5   Chemistry Department, Kiev National Taras Shevchenko University, Kiev, Ukraine
,
Alexey Dobrydnev 
5   Chemistry Department, Kiev National Taras Shevchenko University, Kiev, Ukraine
› Author AffiliationsSupported by: Ministry of Education and Science of Ukraine
Supported by: Enamine Ltd.
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Herein, we report an efficient strategy for the synthesis of C5-functionalized 1-(hetero)aryl-1,2-thiazine 1-oxides (in other words C5-functionalized six-membered endocyclic sulfoximines) based on the CSIC reaction. The starting compounds are readily available 2,2-disubstituted 3-bromopropanenitriles and imino(methyl)(hetero/aryl)-λ6-sulfanones. The reaction can be performed in a one-pot fashion. The method worked well and provided previously unreported spirocyclic and S-heteroaryl substituted 1,2-thiazine 1-oxides. These compounds were designed as multi-target small molecules and a preliminary in silico study indicated their good binding affinity to CLK4 and MAO B – the receptors associated with cancer and neurodegenerative diseases.



Publication History

Received: 28 February 2025

Accepted after revision: 07 May 2025

Accepted Manuscript online:
07 May 2025

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