| 多取代芳香族化合物的合成 5.卤素-苯硒基取代的丁二烯和丁炔二酸二甲酯的环加成-芳构化串连反应 |
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| 引用本文： | 韩广甸,黄国锋.多取代芳香族化合物的合成 5.卤素-苯硒基取代的丁二烯和丁炔二酸二甲酯的环加成-芳构化串连反应[J].合成化学,1997(2). |
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| 作者姓名： | 韩广甸 黄国锋 |
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| 作者单位： | 中国医学科学院中国协和医科大学药物研究所 |
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| 摘 要： | 本文报道用环加成－芳构化串连反应制备多取代芳香族化合物的方法。将１－氯－２－卤－３－苯硒基－１，３－丁二烯（５）与丁炔二酸二甲酯进行Ｄｉｅｌｓ－Ａｌｄｅｒ反应时，能直接生成多取代的芳香族化合物４－苯硒基－５－卤代邻苯二甲酸二甲酯（４）。若用２－卤素－３－苯硒基－１，３－丁二烯（１）与丁炔二酸二甲酯进行Ｄｉｅｌｓ－Ａｌｄｅｒ反应，只得到正常的加成产物４－苯硒基－５－卤素－１，４－环己二烯－１，２－二甲酸二甲酯（３），需再用ＤＤＱ处理，才得到多取代芳香族化合物（４）。
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| 关 键 词： | 多取代芳香族化合物 合成 DDQ脱氢 Diels－Alder反应 环加成－芳构化串连反应 |
Synthesis of Polysubstituted Aromatic Compounds 5. The Tandem Cycloaddition Aromatization Reaction of Halogen Phenylseleno Substituted Butadiene with Dimethyl Acetylenedicarboxylate |
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| Han,Guang Dian Huang,Guo Feng.Synthesis of Polysubstituted Aromatic Compounds 5. The Tandem Cycloaddition Aromatization Reaction of Halogen Phenylseleno Substituted Butadiene with Dimethyl Acetylenedicarboxylate[J].Chinese Journal of Synthetic Chemistry,1997(2). |
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| Authors: | Han Guang Dian Huang Guo Feng |
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| Abstract: | The synthesis of polysubstituted aromatic compounds by using tandem cycloaddition aromatization reaction was reported. 1 Chloro 2 halo 3 phenylseleno 1,3 butadiene (5) was reacted with dimethyl acetylenedicarboxylate, the dimethyl 4 phenylseleno 5 halo o phthalate (4) was afforded directly. In the case of 2 halo 3 phenylseleno 1,3 butadiene (1) with dimethyl acetylenedicarboxylate, the polysubstituted aromatic compound (4) was prepared via the Diels Alder reaction followed by DDQ dehydrogenation. |
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| Keywords: | Polysubstituted aromatic compound Synthesis DDQ dehydrogenation Diels Alder reaction Tandem cycloaddition aromatization reaction |
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