Articles

Copper-Catalyzed Microwave-Assisted Synthesis of Benzothiazole Derivatives in Water

  • Ke Fang ,
  • Wu Wen ,
  • Lin Chen ,
  • Li Peng
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  • a Department of Pharmacy, Fujian Medical University, Fuzhou 350004;
    b Xiamen Maternity and Child Care Hospital, Xiamen 361003

Received date: 2013-06-30

  Revised date: 2013-07-17

  Online published: 2013-08-13

Supported by

Project supported by the National Natural Science Foundation of China (No. 81202560) and the Natural Science Foundation of Fujian Province (No. 2012J05150).

Abstract

A simple, efficient, inexpensive and powerful microwave-assisted method for the coupling of 2-iodoanilines with aldehydes was developed by using cheap CuI as catalyst, inexpensive and readily available 8-hydroxyquinoline as ligand, water as solvent at 100 ℃. Most target products were obtained in high yields.

Cite this article

Ke Fang , Wu Wen , Lin Chen , Li Peng . Copper-Catalyzed Microwave-Assisted Synthesis of Benzothiazole Derivatives in Water[J]. Chinese Journal of Organic Chemistry, 2013 , 33(12) : 2559 -2564 . DOI: 10.6023/cjoc201306044

References

[1] Hofmann, A. W. Ber. Dtsch. Chem. Ges. 1879, 12, 1126.

[2] (a) Aiello, S.; Wells, G.; Stone, E. L.; Kadri, H.; Bazzi, R.; Bell, D. R.; Stevens, M. F. G.; Matthews, C. S.; Bradshaw, T. D.; Westwell, A. D. J. Med. Chem. 2008, 51, 5135.

(b) Delmas, F.; Di, G. C.; Robin, M.; Azas, N.; Gasquet, M.; Detang, C.; Costa, M.; Timon-David, P.; Galy, J.-P. Antimicrob. Agents Chemother. 2002, 46, 2588.

(c) Waisser, K.; Jozova, M.; Odlerova, Z. Folia Pharm. Univ. Carol. 1995, 19, 79.

(d) Stevens, M. F. G.; Slli, D. F.; Castro, A. J. Chem. Soc., Perkin Trans. 1 1996, 83.

(e) Shi, D. F.; Bradshaw, T. D.; Wrigley, S.; McCall. C. J.; Lelieveld, P.; Fichtner, I.; Stevens, M. F. G. J. Med. Chem. 1996, 39, 3375.

(f) Bunnett, J. F.; Hrutfiord, B. F. J. Am. Chem. Soc. 1961, 83, 1691.

[3] Song, J. H.; Huang, C. S.; Nagata, K.; Yeh, J. Z.; Narahashi, T. J. Pharmacol. Exp. Ther. 1997, 282, 707.

[4] (a) Terashima, M.; Ishii, M.; Kanaoka, Y. Synthesis 1982, 484.

(b) Hein, D. W.; Alheim, R. J.; Leavitt, J. J. J. Am. Chem. Soc. 1957, 79, 427.

(c) Bougrin, K.; Loupy, A.; Soufiaoui, M. Tetrahedron 1998, 54, 8055.

(d) Tale, R. H. Org. Lett. 2002, 4, 1641.

(e) Couture, A.; Grandclaudon, P. Heterocycles 1984, 22, 1383.

(f) Liu, J.; Liu, Q.; Xu, W.; Wang, W. Chin. J. Chem. 2011, 29, 1739.

(g) Brembilla, A.; Roizard, D.; Lochon, P. Synth. Commun. 1990, 20, 3379.

(h) Sawhney, S. N.; Sharma, P.; Bajaj, K.; Gupta, A. Synth. Commun. 1993, 23, 263.

[5] (a) Park, N.; Heo, Y.; Kumar, M. R.; Kim, Y.; Song, K. H.; Lee, S. Eur. J. Org. Chem. 2012, 1984.

(b) Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Heterocycles 2004, 63, 2769.

[6] Ma, D.; Xie, S.; Xue, P.; Zhang, X.; Dong, J.; Jiang, Y. Angew. Chem., Int. Ed. 2009, 48, 4222.

[7] Qiu, J.; Zhang, X.; Tang, R.; Zhong, P.; Li, J. Adv. Synth. Catal. 2009, 351, 2319.

[8] Weng, J.; Huang, H.; Tan, C.; Liu, X.; Chu, W.; Chen, J. Chin. J. Org. Chem. 2012, 32, 957 (in Chinese). (翁建全, 黄华, 谭成侠, 刘幸海, 储为盛, 陈杰, 有机化学, 2012, 32, 957.)

[9] Wang, Z.; Tang, R.; Li, J. Chin. J. Chem. 2011, 29, 314.

[10] (a) Shen, G.; Lv, X.; Bao, W. Eur. J. Org. Chem. 2009, 5897.

(b) Murru, S.; Ghosh, H.; Sahoo, S. K.; Patel, B. K. Org. Lett. 2009, 11, 4254.

[11] (a) Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275.

(b) Li, C.-J. Chem. Rev. 2005, 105, 3095.

(c) Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563.

(d) Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.

[12] (a) Ranu, B. C.; Jana, R.; Dey, S. S. Chem. Lett. 2004, 33, 274.

(b) Raju, B. C.; Theja, N. D.; Kumar, J. A. Synth. Commun. 2009, 39, 175.

(c) Head-Gordon, T.; Hura, G. Chem. Rev. 2002, 102, 2651.

[13] Deng, H.; Li, Z.; Ke, F.; Zhou, X. Chem. Eur. J. 2012, 18, 4840.

[14] (a) Li, Z.; Wang, L.; Zhou X. Adv. Synth. Catal. 2012, 354, 584.

(b) Zhang, J.; Yin, H.; Han, S. Chin. J. Org. Chem. 2012, 32, 1429 (in Chinese). (张敬先, 殷慧清, 韩世清, 有机化学, 2012, 32, 1429.)

[15] Zhang, L.; Liu, J.; Wang, Y. Chin. J. Org. Chem. 2013, 33, 339 (in Chinese). (张丽君, 刘巨艳, 王英, 有机化学, 2013, 33, 339.)

[16] Ding, Q. P.; Huang, X. G.; Wu, J. J. Comb. Chem. 2009, 11, 1047.

[17] Poronik, Y.; Yakubovskyi, V. P.; Shandura, M. P.; Vlasenko, Y. G.; Chernega, A. N.; Kovtun, Y. P. Eur. J. Org. Chem. 2010, 2746.

[18] Burger, A.; Sawhney, S. N. J. Med. Chem. 1968, 11, 270.

[19] Roe, A.; Tucker, W. P. J. Heterocycl. Chem. 1965, 2, 148.

[20] Lim, H. J.; Myung, D.; Lee, I. Y. C.; Jung, M. H. J. Comb. Chem. 2008, 10, 501.

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