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Synthesis of 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones and their reactions with aromatic 1,2-diamines, hydrazine and hydroxylamine
Tetrahedron ( IF 2.1 ) Pub Date : 2015-10-06 21:49:38
Alexander V. Safrygin, Roman A. Irgashev, Pavel A. Slepukhin, Gerd-Volker Röschenthaler, Vyacheslav Y. Sosnovskikh

2-(Trifluoromethyl)furanones were obtained in good yields via the Claisen condensation of acetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. These compounds react with 2,3-diaminopyridine, o-phenylenediamine and 2,3-diaminonaphthalene in refluxing acetic acid to give the corresponding quinoxaline derivatives, the regioisomeric and tautomeric composition of which was investigated. Reactions of 2-(trifluoromethyl)furanones with hydrazines and hydroxylamine proceeded regioselectively and gave pyridazine, pyrazole and isoxazole derivatives in high yields. Their regiochemistry was established by X-ray diffraction analysis.

中文翻译:

5-芳基-2-羟基-2-(三氟甲基)呋喃-3(2H)-的合成及其与芳族1,2-二胺,肼和羟胺的反应

通过苯乙酮与2-甲氧基四氟丙酸甲酯的克莱森缩合,然后用硫酸介导的反应产物脱保护,以高收率获得了2-(三氟甲基)呋喃酮。这些化合物与2,3-二氨基吡啶,邻苯二胺和2,3-二氨基萘在回流的乙酸中反应,得到相应的喹喔啉衍生物,研究了它们的区域异构和互变异构组成。2-(三氟甲基)呋喃酮与肼和羟胺的反应区域选择性地进行,并以高收率得到哒嗪,吡唑和异恶唑衍生物。通过X射线衍射分析确定了它们的区域化学。
更新日期:2015-10-07
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