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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
引用本文:史达清,王菊仙,荣良策,庄启亚,胡宏纹.低价钛引起的邻硝基苯甲酰胺与酮的还原成环反应[J].高等学校化学学报,2004,25(3):462-465.
作者姓名:史达清  王菊仙  荣良策  庄启亚  胡宏纹
作者单位:1. 徐州师范大学化学系,徐州221009;南京大学化学系,南京210093
2. 徐州师范大学化学系,徐州221009
3. 南京大学化学系,南京210093
基金项目:江苏省教育厅自然科学基金 (批准号 :0 0 KJB15 0 0 0 8)资助
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
文章编号:0251-0790(2004)03-0462-04
收稿时间:2003-01-29
修稿时间:2003年1月29日

Low-valent Titanium Induced Reductive Cyclization of o-Nitrobenzamides and Ketones
SHI Da Qing ,WANG Ju Xian ,RONG Liang Ce ,ZHUANG Qi Ya ,HU Hong Wen.Low-valent Titanium Induced Reductive Cyclization of o-Nitrobenzamides and Ketones[J].Chemical Research In Chinese Universities,2004,25(3):462-465.
Authors:SHI Da Qing    WANG Ju Xian  RONG Liang Ce  ZHUANG Qi Ya  HU Hong Wen
Institution:SHI Da Qing 1,2*,WANG Ju Xian 1,RONG Liang Ce 1,ZHUANG Qi Ya 1,HU Hong Wen 2
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.
Keywords:Low  valent titanium  o    Nitrobenzamide  1  2  Dihydroquinazolin  4(3H)  one  
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