Synthesis of fused thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels-Alder reaction related tandem and domino processes

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• 作者：Nataliya Zelisko^a ; Dmytro Atamanyuk^a ; ^&dagger ; ; Yuri Ostapiuk^b ; Andriy Bryhas^b ; Vasyl Matiychuk^b ; Andrzej Gzella^c ; Roman Lesyk^a ; ^{dr_r_lesyk@org.lviv.net" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Thiopyrano[2 ; 3-d][1 ; 3]thiazoles ; hetero-Diels&ndash ; Alder reaction ; Tandem and domino reactions
• 刊名：Tetrahedron
• 出版年：2015
• 出版时间：16 December 2015
• 年：2015
• 卷：71
• 期：50
• 页码：9501-9508
• 全文大小：1098 K

文摘

Various novel rel-(5R,5aR,11bS)-2,6-dioxo-3,5a,6,11b-tetrahydro-2Н,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-5-carboxylic acid derivatives were synthesized via hetero-Diels–Alder reaction related acylation-based tandem processes of 5-(ortho-hydroxybenzylidene)-substituted 4-thioxo-2-thiazolidinones with fumaric and maleic acid derivatives. The structurally similar rel-(5aR,5R,11bR) derivatives were synthesized via domino reaction of isorhodanine and (2E)-4-(2-formylphenoxy)but-2-enoates. The stereochemistry of cycloadditions was confirmed by NMR spectra and a single crystal X-ray diffraction analysis.