SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 07: 1241 - 1246

DOI: https://doi.org/10.6023/cjoc201203011

Full Papers

Synthesis and Fungicidal Activity of Novel 3-(1,3,4-Thiadiazolyl)-1,3-bezoxazines

  • Tang Zilong ,
  • Chang Shuhong ,
  • Yan Lin ,
  • Cui Meiyan ,
  • Liu Hanwen
Expand
  • a Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, XiangTan 411201;
    b School of Chemistry and Chemical Engineering, Hunan University of Science and Technology,Xiangtan 411201;
    c Jiangxi Dongbang Pharmaceutical Co. Ltd., Fengxin 330700

Received date: 2012-03-27

  Revised date: 2012-05-05

  Online published: 2012-05-16

Supported by

Project supported by the National Natural Science Foundation of China (No. 21042011), Scientific Research Fund of Hunan Provincial Education Department (No. 10A034) and Hunan Provincial Postdoctoral Science Foundation (No. 2010RS4033) for the financial support of this work.

Fold

Abstract

A series of novel 3-(1,3,4-thiadiazolyl)-1,3-benzoxazines were prepared in 47-62% yields from 2-(1,3,4-thiadiazolyl-2-aminomethyl)phenols and CH2Cl2 by phase transfer catalysis reaction for the first time. It was investigated the amount of phase transfer catalyst and reactants, temperature on the yield of the reaction. The structures of the products were characterized by FT-IR, 1H NMR, 13C NMR and elemental analysis. The fungicidal activities of the prepared compounds were also preliminarily evaluated. Most of them displayed moderate fungicidal activity.

Key words： 1,3,4-thiadiazolyl-1,3-benzoxazine; phase transfer catalysis reaction; synthesis; fungicidal activity

Cite this article

Tang Zilong , Chang Shuhong , Yan Lin , Cui Meiyan , Liu Hanwen . Synthesis and Fungicidal Activity of Novel 3-(1,3,4-Thiadiazolyl)-1,3-bezoxazines[J]. Chinese Journal of Organic Chemistry, 2012 , 32(07) : 1241 -1246 . DOI: 10.6023/cjoc201203011

References

[1] Mireya, E. R.; Carrajal, M.A.; Rincon, J. M. Rev. Colomb. Cienc. Quim.-Farm., 1980, 3, 63.
[2] Gomez, P. G.; Pabon, H. P.; Carvajal, M. A.; Rincon, J. M. Rev. Colomb. Cienc. Quim.-Farm. 1985, 8, 15.
[3] Waisser, K.; Gregor, K.; Kubicova, L.; Klimesova, V.; Kunes, J.; Machacek, M.; Kaustova, J. Eur. J. Med. Chem. 2000, 35, 733.
[4] Waisser, K.; Gregor, K.; Dostal, H.; Kunes, J.; Kubicova, L.; Klimesova, V.; Kaustova, J. Il Farmaco, 2001, 56, 803.  
[5] Mathiew, B. P.; Kumar. A.; Sharma, S.; Shula, P. K.; Nath, M. Eur. J. Med. Chem. 2010, 45, 1502.
[6] Chylinska, J. B.; Urbanski, T.; Mordarski, M. J. Med. Chem. 1963, 6, 484.  
[7] Bouaziz, Z.; Riondel, J.; Mey, A.; Berlion, M.; Villard, J.; Filliond, H. Eur. J. Med. Chem. 1991, 26, 469.
[8] Benameur, L.; Bouaziz, Z.; Nebois, P.; Bartoli, M-H.; Boitard, M.; Fillion, H. Chem. Pharm. Bull. 1996, 44, 605.  
[9] Wang, S.; Li, Y.; You, Q.; Liu, Y.; Lu, A. Bioorg. Med. Chem. Lett., 2008, 18, 4095.  
[10] Pasternak, A.; Goble, S. D.; Struthers, M.; Vicario, P. P.; Ayala, J. M.; Salvo, J. D.; Kilburn, R.; Wisniewski, T.; DeMartino. J. A.; Mills, S. G.; Yang,L. ACS Med. Chem. Lett., 2010, 1, 14.  
[11] Eva Petrlikova, E.; Waisser, K.; Divisova, H.; Husakova, P.; Vrabcova, P.; Kunes, J.; Kolar, K.; Stolarikova, J. Bioorg. Med. Chem. 2010, 18, 8178.  
[12] Tang, Z.; Chen, W.; Zhu, Z.; Liu, H. J. Heterocyclic Chem., 2011, 48, 255.  
[13] Huang, W.; Zhao, P-L.; Liu, C-L.; Chen, Q.; Liu, Z-M.; Yang, G-F. J. Agric. Food. Chem. 2007, 55, 3004.  
[14] Cao, S.; Wei, N.; Zhao, C.; Li, L.; Huang, Q. Qian, X. J. Agric. Food. Chem. 2005, 53, 3120.  
[15] Wang, T.; Bing, G.; Zhang, X.; Qin, Z.; Yu, H.; Qin, X.; Dai, H.; Fang, J. Chin. J. Org. Chem. 2009, 29, 1287 (in Chinese).(王婷婷,邴贵方,张欣,秦振芳,于海波,秦雪,戴红,方建新,有机化学,2009,29,1287.)
[16] Yang, C.; Yang, S.; Song, B.; Hu, D.; Chen, H.; Xue, W.; Jin, L.; Wu, J.; Xu, W.; Bai, S. Chin. J. Org. Chem. 2010, 30, 1327 (in Chinese).(杨超,杨松,宋宝安,胡德禹,陈红军,薛伟,金林红,吴剑,徐伟明,柏松,有机化学,2010,30,1327.)
[17] Burke, W. J. J. Am. Chem. Soc. 1949, 71, 609.  
[18] Burke, W. J.; Ec, K. C.; Murdock, G. J. Am. Chem. Soc. 1954, 76, 1677.  
[19] Rivera, A.; Ospina, E.; Sanchez, A.; Joseph-Nathan, P. Heterocycles, 1986, 24, 2507.  
[20] McDonagh, A. F.; Smith, H. E. J. Org. Chem. 1968, 33, 1.  
[21] Neuvonen, K.; Pihlaja, K. J. Chem. Soc. Perkin. Trans.II, 1988, 461.
[22] Colin, J. L.; Loubinoux, B. Tetrahedron Lett. 1982, 23, 4245
[23] Campi, E. M.; Jackson, W. R.; McCubbin, Q. J.; Trnacek, A. E. J. Chem. Soc. Chem. Commun. 1994, 2763.
[24] Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-Transfer Catalysis; Chapman & Hall: New York, 1994.
[25] Sasson, Y., Neumann, R., Eds. Handbook of Phase-Transfer Catalysis; Blackie Academic & Professional: London, 1997.
[26] Palmieri, G. Eur. J. Org. Chem. 1999, 805.
[27] Tang, Z.; Chang, S.; Yan, L.; Zhang, C. Liu, H. Chin. J. Applied Chem. 2012 (in Chinese, in press).(唐子龙,常书红,颜林,张超逸,刘汉文,应用化学,2012 (已排版)).
[28] Liu, A.; Ou, X.; Huang, M.; Wang, X.; Liu, X.; Wang, Y.; Chen, C.; Yao, J. Pest Manage Sci, 2005, 61, 166.  
Options
Outlines

/

〈 〉