高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

低价钛促进的苯并咪唑并[1,2-c]喹唑啉衍生物的合成

史达清1,2, 李正义2, 窦国兰2, 石春玲2, 王香善2, 纪顺俊1   

    1. 苏州大学化学化工学院, 江苏省有机合成重点实验室, 苏州 215123;
    2. 徐州师范大学化学系, 徐州 221116
  • 收稿日期:2007-01-24 修回日期:1900-01-01 出版日期:2007-10-10 发布日期:2007-10-10
  • 通讯作者: 史达清

Synthesis of Benzoimidazo[1,2-c]quinazoline Derivatives Promoted by Low-valent Titanium

SHI Da-Qing1,2*, LI Zheng-Yi2, DOU Guo-Lan2, SHI Chun-Ling2, WANG Xiang-Shan2, JI Shun-Jun1   

    1. College of Chemistry and Chemical Engineering, Key Laboratory of Organic Synthesis of Jiangsu Province, Suzhou University, Suzhou 215123, China;
    2. Department of Chemistry, Xuzhou Normal University, Xuzhou 221116, China
  • Received:2007-01-24 Revised:1900-01-01 Online:2007-10-10 Published:2007-10-10
  • Contact: SHI Da-Qing

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摘要： 利用低价钛试剂促进的2-邻硝基苯基苯并咪唑与原甲酸酯或丙酮或固体光气的反应, 合成了一系列苯并咪唑并[1,2-c]喹唑啉衍生物, 化合物的结构经IR, 1H NMR, MS和元素分析确定, 化合物4c的结构经单晶X射线衍射分析进一步确证. 该方法具有原料易得、操作简便和产率高等优点.

关键词: 低价钛, 苯并咪唑并[1,2-c]喹唑啉, 2-邻硝基苯并咪唑

Abstract: Quinazoline is an important heterocyclic compound which has potential biological and pharmaceutical activities. It was reported that benzimidazo[1,2-c]quinazoline derivatives have a high anticancer activity. In this paper, a series of benzimidazo[1,2-c]quinazoline derivatives such as benzimidazo[1,2-c]quinazoline, 5,6-dihydrobenzimidazo[1,2-c]quinazoline and benzimidazo[1,2-c]quinazolin-5-one were synthesized via the reaction of 2-(o-nitrophenyl)benzimidazoles with triethyl orthoformate or acetone or triphosgene promoted by the low-valent titanium reagent(TiCl4-Zn system). The products were characterized via IR, 1H NMR, MS and elemental analysis. The structure of compound 4c was confirmed by X-ray single crystal diffraction. A possible reaction mechanism was put forward in this paper. This new method possesses the advantages of easily accessible starting materials, convenient manipulation and high yields.

Key words: Low-valent titanium, Benzimidazo[1,2-c]quinazoine, 2-(o-Nitrophenyl)benzimidazole

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