V. E. Opryshko, A. Yu. Smirnov, Yu. A. Bogdanova, A. A. Mikhaylov, S. A. Krasnova, D. I. Rudik, A. R. Romanenko, A. A. Korlyukov, M. S. Baranov, D. S. Ivanov, “Cycloaddition of 2-mercaptobenzaldehyde with 5-arylidene-2-thioxooxazolidin-4-ones”, Mendeleev Commun., Mi mendc7462

Communications

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

V. E. Opryshko^a, A. Yu. Smirnov^ab, Yu. A. Bogdanova^ab, A. A. Mikhaylov^ab, S. A. Krasnova^a, D. I. Rudik^a, A. R. Romanenko^c, A. A. Korlyukov^c, M. S. Baranov^ab, D. S. Ivanov^a

^a M. M. Shemyakin–Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117997 Moscow, Russian Federation
^b N. I. Pirogov Russian National Research Medical University, 117997 Moscow, Russian Federation
^c A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119334 Moscow, Russian Federation

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.

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

Received: 01.11.2025
Accepted: 28.01.2026

Language: English

DOI: 10.71267/mencom.7959