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Reactions of thiiranes with NH-heterocycles 1. An investigation of the reaction of 2-chloromethylthiirane with 3,5-dibromo-4-nitropyrazole
Chemistry of Heterocyclic Compounds ( IF 1.4 ) Pub Date : 2020-10-19 , DOI: 10.1007/s10593-020-02800-7
Ferkat А. Khaliullin , Elena E. Klen , Nadezhda N. Makarova , Svetlana O. Shepilova , Irina P. Baikova

The reaction of 2-chloromethylthiirane with 3,5-dibromo-4-nitropyrazole in H2O and the aprotic solvent MeCN in the presence of bases was investigated. It was found that thiirane-thietane rearrangement occurs in an aqueous medium with the formation of 3,5-dibromo-4-nitro-1-(thietan-3-yl)-1H-pyrazole. In MeCN, 3,5-dibromo-4-nitro-1-(thiiran-2-ylmethyl)-1H-pyrazole and the product of its reaction with the starting pyrazole, 6-bromo-2-[(3,5-dibromo-4-nitro-1H-pyrazol-1-yl)methyl]-7-nitro-2,3-dihydropyrazolo[5,1-b]thiazole, are formed, the yields of which depend on the molar ratio of the reactants.



中文翻译:

硫杂环丁烷与NH-杂环的反应1. 2-氯甲基噻喃与3,5-二溴-4-硝基吡唑的反应研究

在碱的存在下,研究了2-氯甲基噻喃与3,5-二溴-4-硝基吡唑在水中和非质子传递溶剂MeCN的反应。发现在水介质中发生硫杂环丁烷-硫杂环丁烷重排,并形成3,5-二溴-4-硝基-1-(噻吩-3-基)-1 H-吡唑。在MeCN中,3,5-二溴-4-硝基-1-(噻喃-2-基甲基)-1 H-吡唑及其与起始吡唑的反应产物6-溴-2-[(3,5-形成了二溴-4-硝基-1 H-吡唑-1-基)甲基] -7-硝基-2,3-二氢吡唑并[5,1- b ]噻唑,其产率取决于其的摩尔比。反应物。

更新日期:2020-10-19
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