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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (10): 1690-1694. 上一篇    下一篇

研究简报

10,10-二吡啶甲基-9,10-二氢蒽的合成研究

张红1,2，刘文杰2，曹德榕*,1，江焕峰1   

  1. (1华南理工大学化学化工学院 广州 510640)
    (2广东药学院医药化工学院 广州 510006)
  • 收稿日期:2011-02-20 修回日期:2011-05-02 发布日期:2011-05-06
  • 通讯作者: 曹德榕 E-mail:drcao@scut.edu.cn

Synthesis of 10,10-Bispyridinylmethyl-9,10-dihydroanthracenes

Zhang Hong1,2 Liu Wenjie1 Cao Derong*,1 Jiang Huanfeng1   

  1. (1 School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640)
    (2 School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Guangzhou 510006)
  • Received:2011-02-20 Revised:2011-05-02 Published:2011-05-06
  • Contact: Derong Cao E-mail:drcao@scut.edu.cn

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被引次数

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蒽酮1和氯甲基吡啶盐酸盐2在甲苯中回流反应生成10,10-二吡啶甲基-9(10H)蒽酮(3), 收率63%～68%|3用硼氢化钠还原生成10,10-二吡啶甲基-9,10-二氢蒽-9-醇(4), 收率87%～90%|蒽醇4在酸催化下发生歧化反应, 得到还原产物10,10-二吡啶甲基-9,10-二氢蒽(5)和氧化产物蒽酮3. 该歧化反应受催化剂、溶剂和反应温度等影响. 当蒽醇4用三氟化硼为催化剂、甲苯为溶剂、回流反应, 5的收率达到74%. 所合成的新化合物都经1H NMR, 13C NMR, MS和元素分析表征确认.

关键词: 10,10-二吡啶甲基-9,10-二氢蒽, 10,10-二吡啶甲基-9(10H)蒽酮, 10,10-二吡啶甲基-9,10-二氢蒽-9-醇, 歧化反应, 三氟化硼

Anthrone 1 and picolyl chloride hydrochloride 2 reacted in refluxing toluene for 2 h to give 10,10-bispyridinylmethyl-9(10H)-anthrones (3) in 63%～68% yields. Reduction of 3 with NaBH4 at 80 ℃ afforded 10,10-bispyridinylmethyl-9,10-dihydroanthracen-9-ols (4) in 87%～90% yields. The disproportionation reaction of 4 with acid as catalyst gave the reduced product, 10,10-bispyridinylmethyl-9,10-dihy- droan-thracenes (5) and the oxidized product, anthrones 3. The disproportionation reaction was influenced by catalyst, solvent and reaction temperature. When 4 was catalyzed by BF3 in refluxing toluene, the highest yield of 5 was up to 74%. The structures of all new compounds were confirmed by 1H NMR, 13C NMR, MS techniques and elemental analysis.

Key words: 10,10-bispyridinylmethyl-9,10-dihydroanthracenes, 10,10-bispyridinylmethyl-9(10H)-anth- rones, 10,10-bispyridinylmethyl-9,10-dihydroanthracene-9-ols, disproportionation, BF3