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Facile synthesis of fused polyheterocycles containing trifluromethylated benzo[6,7]chromeno[2,3-c]pyrazoles via one-pot two-step MCRs
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2020-04-28 , DOI: 10.1016/j.jfluchem.2020.109525
Wenwen Duan , Zeyu Li , Fanhui Chen , Min Zhang , Hongmei Deng , Liping Song

A series of non-annulated products: trifluoromethylpyrazolone-tethered trisubstituted methane derivatives were synthesized in high yields in acetonitrile solvent catalyzed by NH4OAc via one-pot, three-component reactions of 2-hydroxy-1,4-naphthoquinone, aromatic aldehydes and 1-aryl-3-trifluoromethyl-5-pyrazolone. Treatment of trifluoromethylpyrazolone-tethered trisubstituted methane derivatives with the dehydrating agent SOCl2/Pyridine in acetonitrile afforded the corresponding annulated fused polyheterocyclic products trifluoromethylated benzo[6,7]chromeno[2,3-c]pyrazole-5,10-dione derivatives. Furthermore, an efficient, straightforward protocol has been developed for the synthesis of trifluoromethylated benzo[6,7]chromeno[2,3-c]pyrazole-5,10-dione derivatives at medium yields via one-pot, two-step, three-component reactions. Meanwhile, the structures of typical products were further confirmed by XRD-analysis.



中文翻译:

通过一锅两步MCR轻松合成含三氟甲基化苯并[6,7]铬[2,3- c ]吡唑的稠合多杂环

通过NH 4 OAc催化的2-羟基-1,4-萘醌,芳香醛和三元醇的一锅,三组分反应,在乙腈溶剂中高收率合成了一系列非环状产物:三氟甲基吡唑啉酮系链的三取代甲烷衍生物。1-芳基-3-三氟甲基-5-吡唑酮。用脱水剂SOCl 2 /吡啶在乙腈中处理三氟甲基吡唑啉酮连接的三取代甲烷衍生物,得到相应的环合稠合多杂环产物,三氟甲基化苯并[6,7] chromeno [2,3 - c ]吡唑-5,10-二酮衍生物。此外,已经开发了一种有效,简单的方法来合成三氟甲基化的苯并[6,7]铬[2,3- c一锅,两步,三组分反应以中等收率得到]吡唑-5,10-二酮衍生物。同时,通过XRD分析进一步证实了典型产品的结构。

更新日期:2020-04-28
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