Synthesis of 2-Ester-substituted-1,5-benzoxazepines and Studies on the By-product in the Reaction

doi:10.6023/cjoc201205034

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2122-2128.DOI: 10.6023/cjoc201205034 Previous Articles Next Articles

Articles

2-酯基-1,5-苯并氧氮杂(艹卓)的合成及反应副产物的研究

刘倩^a, 赵利飞^a, 李文红^b, 李媛^a

a 河北师范大学化学与材料科学学院石家庄 050024;
b 河北工业职业技术学院环境与化学工程系石家庄 050091

收稿日期:2012-05-29 修回日期:2012-07-11 发布日期:2012-07-17
通讯作者: 李媛 E-mail:liyuanhbsd@163.com
基金资助:
国家自然科学基金(No. 20972040)资助项目.

Synthesis of 2-Ester-substituted-1,5-benzoxazepines and Studies on the By-product in the Reaction

Liu Qian^a, Zhao Lifei^a, Li Wenhong^b, Li Yuan^a

a College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050024;
b Environment and Chemical Engineering, Hebei College of Industry and Technology, Shijiazhuang 050091

Received:2012-05-29 Revised:2012-07-11 Published:2012-07-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20972040).

1. Synthesis of 2-Ester-substituted-1,5-benzoxazepines and Studies on the By-product in the Reaction.PDF(1720KB)

Abstract

A series of new 1,5-benzoxazepines have been synthesized from substituted benzene, maleic anhydride and 2-aminophenol (4-chloro-2-aminophenol) and identified by IR, ¹H NMR, MS (HRMS) techniques and elemental analysis. Meanwhile, the structure of one main by-product 2-benzoylmethyl-2H-1,4-benzoxazin-3(4H)-one (6h') was identified, and the possible mechanism of producing the by-product was proposed. The optimization of reaction conditions showed that the reactions were performed in DMF solvent, at refluxed temperature and catalyzed by p-toluenesulfonic acid, and 2-ester-sub-stituted-1,5-benzoxazepines 6 were the main products. While, the reactions were performed in methyl alcohol, at refluxed temperature and catalyzed by acetic acid, and the by-product 6h' was formed in good yield.

Key words: Michael addition, 1,5-benzoxazepine, 2-aminophenol, 4-chloro-2-aminophenol, reaction mechanism

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Liu Qian, Zhao Lifei, Li Wenhong, Li Yuan. Synthesis of 2-Ester-substituted-1,5-benzoxazepines and Studies on the By-product in the Reaction[J]. Chin. J. Org. Chem., 2012, 32(11): 2122-2128.

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2-酯基-1,5-苯并氧氮杂(艹卓)的合成及反应副产物的研究

Synthesis of 2-Ester-substituted-1,5-benzoxazepines and Studies on the By-product in the Reaction

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