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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 11: 2122 - 2128

DOI: https://doi.org/10.6023/cjoc201205034

Articles

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

  • Liu Qian ,
  • Zhao Lifei ,
  • Li Wenhong ,
  • Li Yuan
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  • 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 date: 2012-05-29

  Revised date: 2012-07-11

  Online published: 2012-07-17

Supported by

Project supported by the National Natural Science Foundation of China (No. 20972040).

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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

Cite this article

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]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2122 -2128 . DOI: 10.6023/cjoc201205034

References


[1] Chakravarti, B.; Siddiqui, J. A.; Dwivedi, S. K. D.; Deshpande, S.; Samanta, K.; Bhatta, R. S.; Panda, G.; Prabhaka, Y. S.; Konwar, R.; Sanyal, S.; Chattopadhyay, N. Mol. Cell. Endocrinol. 2011, 338, 68.

[2] Maginn, E. N.; Browne, P. V.; Hayden, P.; Vandenberghe, E.; MacDonagh, B.; Evans, P.; Goodyer, M.; Tewari, P.; Campiani, G.; Butini, S.; Williams, D. C.; Zisterer, D. M.; Lawler, M. P.; McElligott, A. M. Br. J. Cancer 2011, 104, 281.

[3] Zificsak, C. A.; Theroff, J. P.; Aimone, L. D.; Albom, M. S.; Angeles, T. S.; Brown, R. A.; Galinis, D.; Grobelny, J. V.; Herbertz, T.; Husten, J.; Kocsis, L. S.; LoSardo, C.; Miknyoczki, S. J.; Murthy, S.; Rolon-Steele, D.; Underiner, T. L.; Wells-Knecht, K. J.; Worrell, C. S.; Zeigler, K. S.; Dorsey, B. D. Bioorg. Med. Chem. Lett. 2011, 21, 660.

[4] L髉ez-Cara, L. C.; Conejo-Garc韆, A.; Marchal, J. A.; Macchione, G.; Cruz-L髉ez, O.; Boulaiz, H.; Garc韆, M. A.; Rodr韌uez- Serrano, F.; Ram韗ez, A.; Cativiela, C.; Jim閚ez, A. I.; Garc韆-Ruiz, J. M.; Choquesillo-Lazarte, D.; Ar醤ega, A.; Campos, J. M. Eur. J. Med. Chem. 2011, 46, 249.

[5] Bajaj, K.; Archana; Kumar, A. Eur. J. Med. Chem. 2004, 39, 369.

[6] Chandrasekhar, S.; Seenaiah, M.; Kumar, A.; Reddy, C. R.; Mamidyala, S. K.; Kumar, C. G.; Balasubramanian, S. Tetrahedron Lett. 2011, 52, 806.

[7] Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Yoden, T.; Yamagiwa, Y.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Bioorg. Med. Chem. 2000, 8, 393.

[8] Kamei, K.; Maeda, N.; Nomura, K.; Shibata, M.; Ogino, R. K.; Koyama, M.; Nakajima, M.; Inoue, T.; Ohno, T.; Tatsuoka, T. Bioorg. Med. Chem. 2006, 14, 1978.

[9] Miki, T.; Kori, M.; Fujishima, A.; Mabuchi, H.; Tozawa, R.; Nakamura, M.; Sugiyama, Y.; Yukimasa, H. Bioorg. Med. Chem. 2002, 10, 385.

[10] Miki, T.; Kori, M.; Mabuchi, H.; Banno, H.; Tozawa, R.; Nakamura, M.; Itokawa, S.; Sugiyama, Y.; Yukimasa, H. Bioorg. Med. Chem. 2002, 10, 401.

[11] Miki, T.; Kori, M.; Tozawa, R.; Nakamura, M.; Sugiyama, Y.; Yukimasa, H. Chem. Pharm. Bull. 2002, 50(1), 53.

[12] Ichikawa, M.; Yokomizo, A.; Itoh, M.; Sugita, K.; Usui, H.; Shimizu, H.; Suzuki, M.; Terayama, K.; Kanda, A. Bioorg. Med. Chem. 2011, 19, 1930.
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