| A New Approach to Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates： High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Derivative |
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| 作者姓名： | Li Rong WEN Gui Long ZHAO Ming LI Wen Ying QI Xiu Li ZHANG Hua Zheng YANG |
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| 作者单位： | [1]College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042 [2]State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 [3]Ocean Food and Drug Institute, Ocean University of China, Qingdao 266003 |
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| 基金项目： | The project was supported by the Natural Science Foundation of Shandong Province （No. Y2003B01） and NNSFC （No. 20172031）. |
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| 摘 要： | It has been known that pyrazole ring has two main tautomeric isomers1-3as showed in Scheme1.The proton could migrate at the two nitrogen atoms of the pyrazole ring.Taylor E.C.and Purdum W.R.4first reported the synthesis of2as an isomer of2a.And so far,only a few literatures5-6have reported that this pyrazole derivative was in form2a,rather than2,therefore both acylation or alkylation reaction occurred at N-1of2a.But the regiochemistry of the N-substituted product of pyrazole has not been u…
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| 关 键 词： | 吡唑 烃化反应 酰化反应 衍生物 合成方法 X射线衍射 |
| 收稿时间： | 2004-10-12 |
A New Approach to Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Derivative |
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| Li Rong WEN Gui Long ZHAO Ming LI Wen Ying QI Xiu Li ZHANG Hua Zheng YANG.A New Approach to Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Derivative[J].Chinese Chemical Letters,2005,16(9):1161-1164. |
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| Authors: | Li;Rong;WEN;Gui;Long;ZHAO;Ming;LI;Wen;Ying;QI;Xiu;Li;ZHANG;Hua;Zheng;YANG |
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| Abstract: | Two series, totalizing twelve, of new compounds, ethyl 1-aroyl/aroylmethyl-5-methyl-3- methylthiopyrazole-4-carboxylates 5/6, have been synthesized via highly regioselective acylation and alkylation of ethyl 3-methyl-5-methylthio-1H- pyrazole-4-carboxylate 2a with aroyl chloride 3 and alpha-tosyloxysubstitutedacetophenones 4. Unexpected structures of the product have been unambiguously determined by both X-ray crystallographic analysis and 2D NMR. |
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| Keywords: | Pyrazole regioselectivity X-ray crystallographic analysis 2D NMR |
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