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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1423 - 1436

DOI: https://doi.org/10.6023/cjoc201212014

Reviews

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).

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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.

Key words： benzothiazole; 2-aminobenzenethiol; thioformanilides; N-arylthiourea; aromatic disulfides; o-haloaniline

Cite this article

Zhu Ning , Zhang Zhiwei , Gao Min , Han Limin , Suo Quanling , Hong Hailong . New Progress in the Synthesis of 2-Substituent-Benzothiazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1423 -1436 . DOI: 10.6023/cjoc201212014

References

[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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