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Cycloaddition of 2-mercaptobenzaldehyde with 5-arylidene-2-thioxooxazolidin-4-ones

Victoria E Opryshko 1
Victoria E Opryshko
, 
Alexander Yuryevich Smirnov 1, 2
Alexander Yuryevich Smirnov
, 
Yulia A Bogdanova 1, 2
Yulia A Bogdanova
, 
Andrey Andreevich Mikhaylov 1, 2
Andrey Andreevich Mikhaylov
, 
Svetlana A. Krasnova 1
Svetlana A. Krasnova
, 
Daniil I Rudik 1
Daniil I Rudik
,  , 
Alexander Aleksandrovich Korlyukov 3
Alexander Aleksandrovich Korlyukov
, 
Mikhail S. Baranov 1, 2
Mikhail S. Baranov
, 
Dmitrii S Ivanov 1
Dmitrii S Ivanov
10.71267/mencom.7959
Published 4 June 2026 , received 1 November 2025
Communication , Volume 36, Issue 4, 457-459
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Opryshko V. E. et al. Cycloaddition of 2-mercaptobenzaldehyde with 5-arylidene-2-thioxooxazolidin-4-ones // Mendeleev Communications. 2026. Vol. 36. No. 4. pp. 457-459.
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Opryshko V. E., Smirnov A. Y., Bogdanova Y. A., Mikhaylov A. A., Krasnova S. A., Rudik D. I., Romanenko A. R., Korlyukov A. A., Baranov M. S., Ivanov D. S. Cycloaddition of 2-mercaptobenzaldehyde with 5-arylidene-2-thioxooxazolidin-4-ones // Mendeleev Communications. 2026. Vol. 36. No. 4. pp. 457-459.
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TY - JOUR
DO - 10.71267/mencom.7959
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7959
TI - Cycloaddition of 2-mercaptobenzaldehyde with 5-arylidene-2-thioxooxazolidin-4-ones
T2 - Mendeleev Communications
AU - Opryshko, Victoria E
AU - Smirnov, Alexander Yuryevich
AU - Bogdanova, Yulia A
AU - Mikhaylov, Andrey Andreevich
AU - Krasnova, Svetlana A.
AU - Rudik, Daniil I
AU - Romanenko, Alexandr Romanovich
AU - Korlyukov, Alexander Aleksandrovich
AU - Baranov, Mikhail S.
AU - Ivanov, Dmitrii S
PY - 2026
DA - 2026/06/04
PB - Mendeleev Communications
SP - 457-459
IS - 4
VL - 36
ER -
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@article{2026_Opryshko,
author = {Victoria E Opryshko and Alexander Yuryevich Smirnov and Yulia A Bogdanova and Andrey Andreevich Mikhaylov and Svetlana A. Krasnova and Daniil I Rudik and Alexandr Romanovich Romanenko and Alexander Aleksandrovich Korlyukov and Mikhail S. Baranov and Dmitrii S Ivanov},
title = {Cycloaddition of 2-mercaptobenzaldehyde with 5-arylidene-2-thioxooxazolidin-4-ones},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7959},
number = {4},
pages = {457--459},
doi = {10.71267/mencom.7959}
}
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Opryshko, Victoria E., et al. “Cycloaddition of 2-mercaptobenzaldehyde with 5-arylidene-2-thioxooxazolidin-4-ones.” Mendeleev Communications, vol. 36, no. 4, Jun. 2026, pp. 457-459. https://mendcomm.colab.ws/publications/10.71267/mencom.7959.
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Keywords

[4 + 2]-cycloaddition
2-mercaptobenzaldehyde
arylidene azolones
spiro[oxazolidine-5,3'-thiochromane]
tandem Michael/aldol reaction
thiochromane

Abstract

A simple diastereoselective synthesis of 4'-hydroxy-2-thioxospiro[oxazolidine-5,3'-thiochroman]-4-ones comprises the [4 + 2] cycloaddition of 2-mercaptobenzaldehyde with 5-arylidene-3-phenyl-2-thioxooxazolidin-4-ones. In case of DABCO as the base, (2'R*,4'R*,5S*)-diastereomers predominate while L-proline is responsible for (2'R*,4'S*,5S*)-configuration of the products.

Funders

Russian Science Foundation
23-73-10004

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