综述与进展

2-取代苯并噻唑类衍生物合成方法研究的新进展

  • 竺宁 ,
  • 张志伟 ,
  • 高敏 ,
  • 韩利民 ,
  • 索全伶 ,
  • 洪海龙
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  • 内蒙古工业大学化工学院 呼和浩特 010051

收稿日期: 2012-12-11

  修回日期: 2013-01-09

  网络出版日期: 2013-01-11

基金资助

内蒙古自治区自然科学基金(No. 2012MS0204)与内蒙古工业大学科学研究(No. ZD201106)资助项目.

New Progress in the Synthesis of 2-Substituent-Benzothiazole Derivatives

  • Zhu Ning ,
  • Zhang Zhiwei ,
  • Gao Min ,
  • Han Limin ,
  • Suo Quanling ,
  • Hong Hailong
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  • College of Chemical Engineering, Inner Mongolia University of Technolgy, Hohhot 010051

Received date: 2012-12-11

  Revised date: 2013-01-09

  Online published: 2013-01-11

Supported by

Project supported by the Inner Monlia Natural Science Foundation of China (No. 2012MS0204) and the Specialized Research Fund for Key Project of Inner Monlia University of Technology (No. ZD201106).

摘要

2-取代苯并噻唑类衍生物在工业、农业、医药等领域有广泛的应用前景, 因此这类衍生物合成的新方法备受关注. 笔者以邻氨基苯硫酚、芳香邻氨基二硫化物、硫代酰胺、硫脲与邻卤苯胺等反应原料为基础, 从引入硫原子的方法及反应机理的角度综述了近几年合成2-取代苯并噻唑类衍生物的新方法.

本文引用格式

竺宁 , 张志伟 , 高敏 , 韩利民 , 索全伶 , 洪海龙 . 2-取代苯并噻唑类衍生物合成方法研究的新进展[J]. 有机化学, 2013 , 33(07) : 1423 -1436 . DOI: 10.6023/cjoc201212014

Abstract

2-Substituent-benzothiazole derivatives could be widely used in the field of industry, agriculture and medicine. So much attention to the synthetic methods for the synthesis of the benzothiazole derivatives has been attracted and many novel synthetic methods have been developed in recent years. In this review, based on the starting material of 2-aminobenzenethiol, aromatic disulfides, thioformanilides, N-arylthiourea and o-haloaniline, the new synthetic methods for the preparation of the benzothiazole derivatives have been summarized from the introducing methods of the sulfur atom and the reaction mechanism for the formation of benzothiazole derivatives.

参考文献

[1] Hofmann, A. W. Ber. Dtsch. Chem. Ges. 1879, 12, 1126.
[2] Facchinetti, V.; Reis, R. R.; Gomes, C. R. B.; Vasconcelos, T. R. A. Mini-Rev. Org. Chem. 2012, 9, 44.
[3] Weekes, A.; Westwell, A. Curr. Med. Chem. 2009, 16, 2430.
[4] Rahn, N.; Dunkel, R.; Kunz, K.; Peris, G.; Benting, J.; Becker, A.; Voerste, A.; Goergens, U. WO 2010149308, 2010[Chem. Abstr. 2010, 154, 109594].
[5] Dey, S.; Efimov, A.; Giri, C.; Rissanen, K.; Lemmetyinen, H. Eur. J. Org. Chem. 2011, 6226.
[6] Li, Y.; Wang, Y.-L. Chin. J. Org. Chem. 2006, 26, 878 (in Chinese) (李焱, 王玉炉, 有机化学, 2006, 26, 878).
[7] Bahrami, K.; Khodaei, M. M.; Naali, F. J. Org. Chem. 2008, 73, 6835.
[8] Al-Qalaf, F.; Mekheimer, R. A.; Sadek, K. U. Molecules 2008, 13, 2908.
[9] Aliyan, H.; Fazaeli, R.; Fazaeli, N.; Mssah, A. R.; Naghash, H. J.; Alizadeh, M.; Emami, G. Heteroat. Chem. 2009, 20, 202.
[10] Bahrami, K.; Khodaei, M. M.; Naali, F. Synlett 2009, 569.
[11] Cao, K.; Tu, Y. Q.; Zhang, F. M. Sci. China Chem. 2010, 53, 130.
[12] Bandyopadhyay, P.; Sathe, M.; Ponmariappan, S.; Sharma, A.; Sharma, P.; Srivastava, A.; Kaushik, M. Bioorg. Med. Chem. Lett. 2011, 21, 7306.
[13] Bandyopadhyay, P.; Sathe, M.; Prasad, G.; Sharma, P.; Kaushik, M. J. Mol. Catal. A: Chem. 2011, 341, 77.
[14] Mohammadpoor-Baltork, I.; Khosropour, A. R.; Hojati, S. F. Catal. Commun. 2007, 8, 1865.
[15] Liu, J.; Liu, Q.; Xu, W.; Wang, W. Chin. J. Chem. 2011, 29, 1739.
[16] Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. Chin. J. Chem. 2009, 27, 379.
[17] Blacker, A. J.; Farah, M. M.; Hall, M. I.; Marsden, S. P.; Saidi, O.; Williams, J. M. J. Org. Lett. 2009, 11, 2039.
[18] Kenny, R. S.; Mashelkar, U. C. J. Heterocycl. Chem. 2006, 43, 1367.
[19] Yu, Y.; Ni, P.; Lu, T. J. Anhui Normal Univ. 2007, 30, 49.
[20] Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2006, 3715.
[21] Sonika; Meenakshi; Malhotra, R. Synth. Commun. 2011, 41, 136.
[22] Gupta, S. D.; Singh, H. P.; Moorthy, N. Synth. Commun. 2007, 37, 4327.
[23] Maleki, B.; Salehabadi, H. Eur. J. Chem. 2010, 1, 377.
[24] Bahrami, K.; Khodaei, M. M.; Nejati, A. Green Chem. 2010, 12, 1237.
[25] Lim, H. J.; Myung, D.; Lee, I.; Jung, M. H. J. Comb. Chem. 2008, 10, 501.
[26] Khosravi, K.; Kazemi, S. Chin. Chem. Lett. 2012, 23, 61.
[27] Sadjadi, S.; Sepehrian, H. Ultrason. Sonochem. 2011, 18, 480.
[28] Yuan, Y. Q.; Guo, S. R. Synth. Commun. 2011, 41, 2169.
[29] Pratap, U. R.; Mali, J. R.; Jawale, D. V.; Mane, R. A. Tetrahedron Lett. 2009, 50, 1352.
[30] Bose, D. S.; M., I. J. Org. Chem. 2006, 71, 8261.
[31] Bose, D. S.; Idrees, M. Tetrahedron Lett. 2007, 48, 669.
[32] Bose, D. S.; Idrees, M.; Srikanth, B. Synthesis 2007, 819.
[33] Cheng, Y.; Yang, J.; Qu, Y.; Li, P. Org. Lett. 2012, 14, 98.
[34] Inamoto, K.; Hasegawa, C.; Hiroya, K.; Doi, T. Org. Lett. 2008, 10, 5147.
[35] Joyce, L. L.; Batey, R. A. Org. Lett. 2009, 11, 2792.
[36] Inamoto, K.; Hasegawa, C.; Kawasaki, J.; Hiroya, K.; Doi, T. Adv. Synth. Catal. 2010, 352, 2643.
[37] Lee, C. L.; Lam, Y.; Lee, S. Y. Tetrahedron Lett. 2001, 42, 109.
[38] Mortimer, C. G.; Wells, G.; Crochard, J. P.; Stone, E. L.; Bradshaw, T. D.; Stevens, M. F. G.; Westwell, A. D. J. Med. Chem. 2006, 49, 179.
[39] Srogl, J.; Hývl, J.; Révész, Á.; Schröder, D. Chem. Commun. 2009, 3463.
[40] Hyvl, J.; Srogl, J. Eur. J. Org. Chem. 2010, 2849.
[41] Yang, X.; Xu, Y.; Chen, J.; Ding, J.; Wu, H.; Su, W. J. Chem. Res. 2009, 2009, 682.
[42] Wang, Z.; Tang, R.; Xiao, Q. Chin. J. Chem. 2011, 29, 314.
[43] Weekes, A. A.; Bagley, M. C.; Westwell, A. D. Tetrahedron 2011, 67, 7743.
[44] Deligeorgiev, T. G.; Kaloyanova, S.; Vasilev, A.; Vaquero, J. J. Phosphorus, Sulfur, Silicon Relat. Elem. 2010, 185, 2292.
[45] Kizek, R.; Vacek, J.; Trnková, L.; Jelen, F. Bioelectrochemistry 2004, 63, 19.
[46] Zhu, N.; Zhang, F.; Liu, G. J. Comb. Chem. 2010, 12, 531.
[47] Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
[48] Saha, P.; Ramana, T.; Purkait, N.; Ali, M. A.; Paul, R.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 8719.
[49] Jaseer, E. A.; Prasad, D. J. C.; Dandapat, A.; Sekar, G. Tetrahedron Lett. 2010, 51, 5009.
[50] Feng, E.; Huang, H.; Zhou, Y.; Ye, D.; Jiang, H.; Liu, H. J. Comb. Chem. 2010, 12, 422.
[51] Zhu, L.; Zhang, M. J. Org. Chem. 2004, 69, 7371.
[52] Murru, S.; Ghosh, H.; Sahoo, S. K.; Patel, B. K. Org. Lett. 2009, 11, 4254.
[53] Ma, D.; Xie, S.; Xue, P.; Zhang, X.; Dong, J.; Jiang, Y. Angew. Chem., Int. Ed. 2009, 48, 4222.
[54] Ma, D.; Lu, X.; Shi, L.; Zhang, H.; Jiang, Y.; Liu, X. Angew. Chem., Int. Ed. 2011, 50, 1118.
[55] Shi, L.; Liu, X.; Zhang, H.; Jiang, Y.; Ma, D. J. Org. Chem. 2011, 76, 4200.
[56] Wang, F.; Cai, S.; Wang, Z.; Xi, C. Org. Lett. 2011, 13, 3202.
[57] Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11, 587.
[58] Qiu, J. W.; Zhang, X. G.; Tang, R. Y.; Zhong, P.; Li, J. H. Adv. Synth. Catal. 2009, 351, 2319.
[59] Murru, S.; Mondal, P.; Yella, R.; Patel, B. K. Eur. J. Org. Chem. 2009, 5406.
[60] Guo, Y. J.; Tang, R. Y.; Zhong, P.; Li, J. H. Tetrahedron Lett. 2010, 51, 649.
[61] Cano, R.; Ramoón, D. J.; Yus, M. J. Org. Chem. 2011, 76, 654.
[62] Yoshizumi, T.; Tsurugi, H.; Satoh, T.; Miura, M. Tetrahedron Lett. 2008, 49, 1598.
[63] Praveen, C.; Kumar, K. H.; Muralidharan, D.; Perumal, P. Tetrahedron 2008, 64, 2369.
[64] Okimoto, M.; Yoshida, T.; Hoshi, M.; Hattori, K.; Komata, M.; Tomozawa, K.; Chiba, T. Heterocycles 2008, 75, 35.
[65] Chou, C. H.; Yu, P. C.; Wang, B. C. Tetrahedron Lett. 2008, 49, 4145.
[66] Stewart, G. W.; Baxter, C. A.; Cleator, E.; Sheen, F. J. J. Org. Chem. 2009, 74, 3229.
[67] Duan, Z.; Ranjit, S.; Liu, X. Org. Lett. 2010, 12, 2430.
[68] Zhu, J.; Chen, Z.; Xie, H.; Li, S.; Wu, Y. Org. Lett. 2010, 12, 2434.
[69] Fan, X.; He, Y.; Zhang, X.; Guo, S.; Wang, Y. Tetrahedron 2011, 67, 6369.
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