Citraconic acid and its anhydride-based hetero-Diels–Alder reactions in the synthesis of new thiopyrano[2,3-d][1,3]thiazole derivatives

Nataliya Zeliskoa Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Lviv, Ukraine

Olexandr Karpenkob Enamine Ltd., Kyiv, Ukraine

Volodymyr Muzychenkoa Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Lviv, Ukraine

Andrzej Gzellac Department of Organic Chemistry, Poznan University of Medical Sciences, Poznan, Poland

Roman Lesyka Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Lviv, Ukraine;d Department of Public Health, Dietetics and Lifestyle Disorders, Faculty of Medicine, University of Information Technology and Management in Rzeszow, Rzeszow, PolandCorrespondence[email protected]

https://orcid.org/0000-0002-3322-0080

Abstract

Novel rel-(5R,5aR,11bS)-5-methyl-2,6-dioxo-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4΄,3΄:4,5]thiopyrano[2,3-d][1,3]thiazole-5-carboxylic acids were synthesized in 63–72% yields via tandem acylation-hetero-Diels–Alder reaction of 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones with citraconic acid and its anhydride. The regio- and stereochemistry of the process was confirmed by NMR spectral data and a single-crystal X-ray diffraction analysis.

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Citraconic acid and its anhydride-based hetero-Diels–Alder reactions in the synthesis of new thiopyrano[2,3-d][1,3]thiazole derivatives

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Citraconic acid and its anhydride-based hetero-Diels–Alder reactions in the synthesis of new thiopyrano[2,3-d][1,3]thiazole derivatives

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