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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
Synthetic Communications ( IF 1.8 ) Pub Date : 2021-01-04 , DOI: 10.1080/00397911.2020.1867868
Nataliya Zelisko 1 , Olexandr Karpenko 2 , Volodymyr Muzychenko 1 , Andrzej Gzella 3 , Roman Lesyk 1, 4
Affiliation  

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.



中文翻译:

新硫代吡喃并[2,3-d] [1,3]噻唑衍生物的合成中柠檬酸及其酸酐基杂Diels-Alder反应

摘要

新型rel-(5 R,5a R,11b S)-5-甲基-2,6-二氧代-3,5a,6,11b-四氢-2H5H -chromeno [4΄,3΄:4,5]硫代吡喃并[2,3- d ] [1,3]噻唑-5-羧酸通过串联酰化反应合成,产率为63-72%--Diels-5-(2-羟基苄叉)-4-硫代杂-Alder反应2-噻唑烷酮与柠康酸及其酸酐。通过NMR光谱数据和单晶X射线衍射分析证实了该方法的区域和立体化学。

更新日期:2021-03-07
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