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低价钛引起的邻硝基苯甲酰胺与酮的还原成环反应

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

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【作者】 史达清王菊仙荣良策庄启亚胡宏纹

【Author】 SHI Da Qing 1,2* , WANG Ju Xian 1, RONG Liang Ce 1, ZHUANG Qi Ya 1, HU Hong Wen 2 (1. Department of Chemistry, Xuzhou Normal University, Xuzhou 221009, China; 2. Department of Chemistry, Nanjing University, Nanjing 210093, China)

【机构】 徐州师范大学化学系南京大学化学系 徐州221009南京大学化学系南京210093徐州221009南京210093

【摘要】 报道了 Ti Cl4 -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( 3 H) -酮 .产物的结构通过元素分析、IR、 1 H NMR谱和单晶 X射线衍射法确定

【Abstract】 This paper reports the reactions of o nitrobenzamides with ketones induced by titanium reagent(TiCl 4 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 P2 1/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) nm 3, Z=4, D c=1.220 g/cm 3, 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 TiCl 4 Sm system. Our method possesses the advantages of easily accessible starting materials, convenient manipulation and moderate to high yield.

【基金】 江苏省教育厅自然科学基金 (批准号 :0 0 KJB15 0 0 0 8)资助
  • 【文献出处】 高等学校化学学报 ,Chemical Research In Chinese Universities , 编辑部邮箱 ,2004年03期
  • 【分类号】O621.25
  • 【被引频次】6
  • 【下载频次】189
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