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A new domino-Knoevenagel-hetero-Diels-Alder reaction
Authors:Vasyl S. Matiychuk  Mykola D. Obushak  Andrzej Gzella  Yuri V. Ostapiuk
Affiliation:a Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla and Mefodiya 6, Lviv 79005, Ukraine
b Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv 79010, Ukraine
c Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland
Abstract:Various novel 3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazol-2-ones were synthesized in 60-80% yields via domino-Knoevenagel-hetero-Diels-Alder reactions of 4-thioxo-1,3-thiazolidin-2-one with 3,7-dimethyl-6-octenal, 2-allyloxybenzaldehydes and 2-formylphenyl (E)-3-aryl-2-propenoates with base catalysis. The possibility of stereo- and regioselective cycloaddition was investigated.
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