Articles

One-Pot Synthesis of 4(3H)-Quinazolinone under Base Condition

  • Liu Change ,
  • Yu Qiyao ,
  • Tang Jianhong ,
  • Li Jiarong
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  • a School of Chemical Engineering and Environment, Beijing Institude of Technology, Beijjing 100081;
    b School of Chemistry, Beijing Institude of Technology, Beijjing 100081;
    c College of Chemical Engineering, Huaqiao University, Xiamen 362021

Received date: 2011-08-10

  Revised date: 2011-11-21

  Online published: 2012-03-24

Abstract

A series of 4(3H)-quinazolinones 3 were obtained from the one-pot synthesis of available substituted aromatic o-aminonitriles 1 with aldehydes 2 in the present of base. This tandem transformation was included in addition, intramolecular Pinner reaction, Dimroth rearrangement and oxidative dehydrogenation. The structures of products were characterized by 1H NMR, 13C NMR, IR spectra and elemental analysis.

Cite this article

Liu Change , Yu Qiyao , Tang Jianhong , Li Jiarong . One-Pot Synthesis of 4(3H)-Quinazolinone under Base Condition[J]. Chinese Journal of Organic Chemistry, 2012 , (03) : 532 -537 . DOI: 10.6023/cjoc1108102

References

[1] Jackson, J. R.; Patrick, D. R.; Dar, M. M.; Huang, P. S. Nat. Rev.Cancer 2007, 7, 107.  

[2] Wang, K.; Kirichian, A. M.; Al Aowad, A. F.; Adelstein, S. J.; Kassis,A. I. Bioconjugate Chem. 2007, 18, 754.  

[3] Rajveer, C.; Stephenrathinaraj, B.; Kumaraswamy, D.; Sudharshini,S.; Swarnalatha, C.; Rajamanickam, V. Int. J. Pharm. Res. 2010, 2,50.

[4] Ozaki, K.; Yamada, Y.; Oine, T.; Ishizuka, T.; Iwasawa, Y. J. Med.Chem. 1985, 28, 568.  

[5] Kumar, P.; Shrivastava, B.; Pandeya, S. N. Adv. Pharmacol. Toxicol.2010, 11, 77.

[6] Zappala, M.; Grasso, S.; Micale, N.; Zuccala, G.; Menniti, F. S.;Ferreri, G.; De Sarro, G.; De Micheli, C. Bioorg. Med. Chem. Lett.2003, 13, 4427.  

[7] Ogawa, N.; Yoshida, T.; Aratani, T.; Koshinaka, E.; Kato, H.; Ito, Y.Chem. Pharm. Bull. 1988, 36, 2955.  

[8] Hess, H. J.; Cronin, T. H.; Scriabine, A. J. Med. Chem. 1968, 11,130.  

[9] Mohamed, M. S.; Kamel, M. M.; Kassem, E. M. M.; Abotaleb, N.;AbdEI-moez, S. I.; Ahmed, M. F. Eur. J. Med. Chem. 2010, 45,3311.

[10] Hamel, E.; Lin, C. M.; Plowman, J.; Wang, H. K.; Lee, K. H.; Paull,K. D. Biochem. Pharmacol. 1996, 51, 53.  

[11] Zhang, W. G.; Yang, L. M.; Wang, W. G.; Jiang, H. J.; Xu, X. Y.Chem. Reag. 1998, 20, 79 (in Chinese).(张文官, 杨联明, 王文广, 江和金, 徐锡瑛, 化学试剂, 1998,20, 79.)

[12] Ma, Z. Z.; Hano, Y.; Nomura, T.; Chen, Y. J. Heterocycles 1999, 51,1883.  

[13] Ma, Z. Z.; Hano, Y.; Nomura, T.; Chen, Y. J. Bioorg. Med. Chem.Lett. 2004, 14, 1193.  

[14] Cagir, A.; Jones, S. H.; Gao, R.; Eisenhauer, B. M.; Hecht, S. M. J.Am. Chem. Soc. 2003, 125, 13628.  

[15] Liu, J. F.; Ye, P.; Sprague, K.; Sargent, K.; Yohannes, D.; Baldino,C. M.; Wilson, C. J.; Ng, S. C. Org. Lett. 2005, 7, 3363.  

[16] Rahman, A. U.; Sultana, N.; Akhter, F.; Nighat, F.; Choudhary, M. I.Nat. Prod. Lett. 1997, 10, 249.  

[17] Cagir, A.; Jones, S. H.; Gao, R.; Eisenhauer, B. M.; Hecht, S. M. J.Am. Chem. Soc. 2003, 125, 13628.  

[18] Johns, S. R.; Lamberton, J. A. Chem. Commun. 1965, 267.

[19] Heravi, M. M.; Sadjadi, S.; Sadjadi, S.; Oskooie, H. A.; Bamoharram,F. F. Ultrason. Sonochem. 2009, 16, 708.  

[20] Li, D.; Wang, Y. L. Chin. J. Org. Chem. 2006, 26, 878 (in Chinese).(李焱, 王玉炉, 有机化学, 2006, 26, 878.)

[21] Li, F.; Feng, Y. Q.; Meng, Q. Q.; Li, W. H.; Li, Z. M.; Wang, Q. R.;Tao, F. G. ARKIVOC 2007, (i), 40.

[22] Strakovsk, A.; Avotins, F.; Petrova, M. Materialzinatneun LietiskaKimija 2003, 6, 122.

[23] Luo, T. J.; Li, Z. M.; Zhao, W. G.; Fan, Z. J. Chin. J Org. Chem.2002, 22, 741 (in Chinese).(罗铁军, 李正名, 赵卫光, 范志金, 有机化学, 2002, 22, 741.)

[24] Akazome, M.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1993, 58,310.  

[25] Shi, D. Q.; Wang, J. X.; Rong, L. C.; Zhuang, Q. Y.; Hu, H. W.Chem. Res. Chin. Univ. 2004, 25, 462 (in Chinese).(史达清, 王菊仙, 荣良策, 庄启亚, 胡宏纹; 王菊仙, 高等学校化学学报, 2004, 25, 462.)

[26] Tang, J. H.; Shi, D. X.; Zhang, L. J.; Zhang, Q.; Li, J. R. Synth.Commun. 2010, 40, 632.  

[27] Balakumar, C.; Lamba, P.; Kishore, D. P.; Narayana, B. L.; Rao, K.V.; Rajwinder, K.; Rao, A. R.; Shireesha, B.; Narsaiah, B. Eur. J.Med. Chem. 2010, 45, 4904.

[28] Davoodnia, A.; Allameh, S.; Fakhari, A. R.; Tavakoli-Hoseini, N.Chin. Chem. Lett. 2010, 21, 550.  

[29] Roger, R.; Neilson, D. Chem. Rev. 1961, 61, 179.  

[30] Rozhkov, V. Y.; Batog, L. V.; Shevtsova, E. K.; Struchkova, M. I.Mendeleev Commun. 2004, 14, 76.  
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