高等学校化学学报

高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (3): 462.

• 研究论文 • 上一篇    下一篇

低价钛引起的邻硝基苯甲酰胺与酮的还原成环反应

史达清1,2, 王菊仙1, 荣良策1, 庄启亚1, 胡宏纹2   

  1. 1. 徐州师范大学化学系, 徐州 221009;
    2. 南京大学化学系, 南京 210093
  • 收稿日期:2003-01-29 出版日期:2004-03-24 发布日期:2004-03-24
  • 通讯作者: 史达清(1962年出生),男,博士研究生,教授,主要从事有机合成研究.E-mail;dqshi@xznu.edu.cn E-mail:dqshi@xznu.edu.cn
  • 基金资助:

    江苏省教育厅自然科学基金(批准号;00KJB150008)资助

Low-valent Titanium Induced Reductive Cyclization of o-Nitrobenzamides and Ketones

SHI Da-Qing1,2, WANG Ju-Xian1, RONG Liang-Ce1, ZHUANG Qi-Ya1, HU Hong-Wen2   

  1. 1. Department of Chemistry, Xuzhou Normal University, Xuzhou 221009, China;
    2. Department of Chemistry, Nanjing University, Nanjing 210093, China
  • Received:2003-01-29 Online:2004-03-24 Published:2004-03-24

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被引次数

17

摘要： 报道了TiCl4-Sm体系引起的邻硝基苯甲酰胺与酮的反应.研究发现,邻硝基苯甲酰胺与酮还原成环生成1,2-二氢喹唑啉-4(3H)-酮.产物的结构通过元素分析、IR、1HNMR谱和单晶X射线衍射法确定.

关键词: 低价钛, 邻硝基苯甲酰胺, 1, 2-二氢喹唑啉-4(3H)-酮

Abstract: This paper reports the reactions of o nitrobenzamides with ketones induced by titanium reagent(TiCl4 Sm system). The results show that the low valent titanium promoted a novel reductive cyclization of o nitrobenzamides and ketones to give 1,2-dihydroquinazolin-4(3H)-ones. The products were characterized by elementary analysis, IR, 1H NMR and X-ray single crystal diffraction. The crystal of compound 3b belongs to monoclinic system with space group P21/n, a =1.191 7(2)nm, b =0.691 1(1)nm , c =1 782 1(4)nm, β=98.81°, V =1.455 04(5)nm3, Z=4, Dc=1.220 g/cm3, μ =0.077 mm-1 , F (000)=568, and final R =0.043 3 and wR =0.107 6 for reflections [ I>2σ(I) ]. In summary, a series of 1,2-dihydroquinazolin 4(3H) ones was synthesized Via reductive cyclization of o nitrobenzamides with ketones induced by the TiCl4 Sm system. Our method possesses the advantages of easily accessible starting materials, convenient manipulation and moderate to high yield.

Key words: Low valent titanium, o-Nitrobenzamide, 1,2-Dihydroquinazolin-4(3H)-one

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