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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (06): 1029-1034. 上一篇    下一篇

研究论文

型2,3-二氢-3-芳亚甲基-4-芳基-1,5-苯并硫氮杂的合成及表征

杨德保a，杨春a，徐峰a,b，刘方明*,a,b,c   

  1. (a杭州师范大学材料与化学化工学院 杭州 310016)
    (b新疆大学化学化工学院 乌鲁木齐 830046)
    (c杭州师范大学有机硅化学及材料技术教育部重点实验室 杭州 310012)
  • 收稿日期:2007-07-20 修回日期:2008-01-08 发布日期:2008-06-26
  • 通讯作者: 刘方明

Synthesis and Characterization of Novel 2,3-Dihydro-3-arylmethylene-4-aryl-1,5-benzo[b]thiazepine

YANG De-Baoa, YANG Chuna, XU Fenga,b, LIU Fang-Ming*,a,b,c   

  1. (a College of Materials and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036)
    (b College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (c Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education,
    Hangzhou Normal University, Hangzhou 310012)
  • Received:2007-07-20 Revised:2008-01-08 Published:2008-06-26
  • Contact: LIU Fang-Ming

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在盐酸和乙醇存在下, 苯乙酮、多聚甲醛以及N,N-二甲基甲酰胺进行Mannich反应, 得到了Mannich碱; 将其和1,2,4-三唑在水中反应, 得到含有1,2,4-三唑的苯丙酮; 然后, 在哌啶和甲苯存在下, 苯丙酮和苯甲醛进行羟醛缩合, 得到一系列含有1,2,4-三氮唑的查尔酮; 最后, 在三氟乙酸的催化下, 查尔酮和邻氨基硫酚发生亲核取代反应, 然后脱水缩合, 合成了一系列2,3-二氢-3-芳亚甲基-4-芳基-1,5-苯并硫氮杂. 其结构经IR, 1H NMR, MS及元素分析确证.

关键词: 查尔酮, 1,2,4-三唑, 1,5-苯并硫氮杂

In the presence of hydrochloric acid and ethanol, interacotion of acetophenone, paraformaldehyde and N,N-dimethylformamide gave Mannich base. This base reacted with 1,2,4-triazole in water to give propiophenone with 1,2,4-triazole as its inclusion. The propiophenone and benzenecarbaldehyde un-derwent an aldol condensation in the presence of piperidine and toluene to afford a series of chalcone con-taining 1,2,4-triazole. Catalyzed by trifluoroacetic acid, the chalcone and o-aminothiophenol took place nucleophilic substitution reaction, and then occured dehydration to gain a series of 2,3-dihydro-3-arylmethylene-4- aryl-1,5-benzothiazepine, the structures of which were characterized by elemental analysis, IR, 1H NMR and MS techniques.

Key words: 1,2,4-triazole, 1,5-benzo[b]thiazepine, chalcone