| 纳米二氧化钛催化二苯并1,10-菲咯啉衍生物的合成研究 |
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| 引用本文： | 许世虹,陈浩,王坚强,楼庆童,罗书平,吴庆安. 纳米二氧化钛催化二苯并1,10-菲咯啉衍生物的合成研究[J]. 合成化学, 2017, 25(9). DOI: 10.15952/j.cnki.cjsc.1005-1511.2017.09.17028 |
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| 作者姓名： | 许世虹 陈浩 王坚强 楼庆童 罗书平 吴庆安 |
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| 作者单位： | 1. 浙江工业大学绿色合成技术国家重点实验室培育基地,浙江杭州,310014;2. 浙江华义医药有限公司,浙江义乌,322000 |
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| 基金项目： | 国家自然科学基金资助项目 |
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| 摘 要： | 首次报道了纳米TiO_2催化1,2-环己二酮与2-氨基苯甲酰衍生物的串联Friedlander反应,合成了9个二苯并1,10-菲咯啉的衍生物(3a~3i),其中3b,3c,3e~3g和3i为新化合物,其结构经~1H NMR,~(13)C NMR和HRMS(ESI)表征。以6,7-二氢-5,8-二苯基苯并[1,10]菲咯啉(3a)的合成为例,对反应条件进行了优化。最佳反应条件为:锐钛型纳米二氧化钛用量为0.2 eq.,1a与2投料比为2.1∶1,乙腈为溶剂,于80℃反应7 h,收率83%。并对反应机理进行了探讨。
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| 关 键 词： | 1,2-环己二酮 2-氨基苯甲酰衍生物 纳米TiO2 催化 Friedlander反应 1,10-菲咯啉 合成 |
Synthesis of Dibeno[ b,j]-1,10-Phenanthroline Derivatives Catalyzed by Nano Titanium Dioxide |
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| XU Shi-hong,CHEN Hao,WANG Jian-qiang,LOU Qing-tong,LUO Shu-ping,WU Qing-an. Synthesis of Dibeno[ b,j]-1,10-Phenanthroline Derivatives Catalyzed by Nano Titanium Dioxide[J]. Chinese Journal of Synthetic Chemistry, 2017, 25(9). DOI: 10.15952/j.cnki.cjsc.1005-1511.2017.09.17028 |
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| Authors: | XU Shi-hong CHEN Hao WANG Jian-qiang LOU Qing-tong LUO Shu-ping WU Qing-an |
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| Abstract: | Nine dibeno[b,j]-1,10-phenanthroline derivatives(3a～3i, 3b, 3c, 3e～3g, 3i were new compounds) were firstly synthesized by the tandem-Friedlander reaction of 1,2-cyclohexanedione with 2-amino benzoyl derivatives using nano-TiO2 as catalyst . The structures were characterized by 1H NMR, 13C NMR, and HR-MS(ESI).The optimum reaction conditions for the model synthesis of 5,8-diphenyl-6,7-dihydrodibenzo[b,j][1,10]phenanthroline(3a) were obtained as follows:the mole ratio of 1a and 2 was 2.1 :1, anatase titanium dioxide dosage was 0.2 eq., reaction at 80 ℃for 7 h in acetonitrile.The yield of 3a is up to 83％.Moreover, the reaction mechanism was also discussed . |
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| Keywords: | 1,2-cyclohexanedione 2-amino benzoyl derivative nano-TiO2 catalysis Friedlander re-action 1,10-phenanthroline synthesis |
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