Progresses in Syntheses and Applications of Bis-1,2,3-triazoles

doi:10.6023/cjoc201307021

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (1): 92-106.DOI: 10.6023/cjoc201307021 Previous Articles Next Articles

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双-1,2,3-三唑化合物的合成与应用研究进展

霍景沛^a,b, 韦新平^a, 莫广珍^a, 彭湃^a, 钟铭丽^a, 陈任宏^c, 汪朝阳^a

a 华南师范大学化学与环境学院教育部环境理论化学重点实验室广州 510006;
b 华南理工大学化工学院广州 510630;
c 广东食品药品职业学院广州 510520

收稿日期:2013-07-15 修回日期:2013-08-30 发布日期:2013-09-06
通讯作者: 汪朝阳 E-mail:wangzy@scnu.edu.cn
基金资助:
国家自然科学基金（No. 20772035）；广东省高等学校人才引进专项资金（No. 粤财教[2011]431号）；广东省自然科学基金（No. S2011010001556）资助项目.

Progresses in Syntheses and Applications of Bis-1,2,3-triazoles

Huo Jingpei^a,b, Wei Xinping^a, Mo Guangzhen^a, Peng Pai^a, Zhong Mingli^a, Chen Renhong^c, Wang Zhaoyang^a

a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006;
b School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510630;
c Guangdong Food and Drug Vocational College, Guangzhou 510520

Received:2013-07-15 Revised:2013-08-30 Published:2013-09-06
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20772035), the 3rd Talents Special Funds of Guangdong Higher Education (No. Guangdong-Finance-Education [2011]431) and the Natural Science Foundation of Guangdong Province (No. S2011010001556).

As a kind of important N-heterocyclic compounds, bis-1,2,3-triazoles have drawn more and more interest of chemists in different research territories. In order to synthesize symmetric and unsymmetrical bis-1,2,3-triazoles, many synthetic strategies, methods and techniques, such as click reaction-oxidative coupling, the combination of starting materials, the concentration control method, the utilization of different active groups, the protection technique, the control of feed ratio, the use of special reagents, and so on, have been developed recently. Classified as different substrates and synthetic approaches, these research progresses are summarized. At the same time, the new progresses in the applications of bis-1,2,3-triazoles in different fields, including medicinal chemistry, coordination chemistry, chemical sensor, molecular recognition, biochemistry, supramolecular chemistry and surfactant are also mentioned in this review. It is pointed out that how to cleverly design and efficiently synthesize the novel bis-1,2,3-triazoles for some special purpose via the simple general methods is still a great challenge.

Key words: bis-1,2,3-triazoles, synthesis, click reaction, azides, alkynes, progress

Cite this article

Huo Jingpei, Wei Xinping, Mo Guangzhen, Peng Pai, Zhong Mingli, Chen Renhong, Wang Zhaoyang. Progresses in Syntheses and Applications of Bis-1,2,3-triazoles[J]. Chin. J. Org. Chem., 2014, 34(1): 92-106.

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References

[1] Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.

[2] Bonger, K. M.; Hoogendoorn, S.; van Koppen, C. J.; Timmers, C. M.; van der Marel, G. A.; Overkleeft, H. S. ACS Med. Chem. Lett. 2011, 2, 85.

[3] Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853.

[4] Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192.

[5] Service, R. F. Science 2008, 320, 868.

[6] Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928.

[7] Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620.

[8] Xiong, X.-Q.; Chen, H.-X. Chin. J. Org. Chem. 2013, 33, 1437 (in Chinese).

(熊兴泉, 陈会新, 有机化学, 2013, 33, 1437.)

[9] Sokolova, N. V.; Nenajdenko, V. G. RSC Adv. 2013, 3, 16212.

[10] Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.

[11] Angell, Y.; Burgess, K. Angew. Chem., Int. Ed. 2007, 46, 3649.

[12] Kwon, M.; Jang, Y.; Yoon, S.; Yang, D.; Jeon, H. B. Tetrahedron Lett. 2012, 53, 1606.

[13] Gonzalez, J.; Perez, V. M.; Jimenez, D. O.; Lopez-Valdez G.; Corona, D.; Cuevas-Yanez, E. Tetrahedron Lett. 2011, 52, 3514.

[14] Goyard, D.; Praly, J.-P.; Vidal, S. Carbohydr. Res. 2012, 362, 79.

[15] Jur?ek, O.; Cametti, M.; Pontini, M.; Kolehmainena, E.; Rissanen, K. Org. Biomol. Chem. 2013, 11, 4585.

[16] Lei, M.; Song, W.-Z.; Zhan, Z.-J.; Chen, X.-W.; Wang, Y.-G. Chin. J. Org. Chem. 2010, 30, 1854 (in Chinese).

(雷鸣, 宋汪泽, 詹祖金, 陈小微, 王彦广, 有机化学, 2010, 30, 1854.)

[17] Wang, Z.-X.; Zhao, Z.-G. J. Heterocycl. Chem. 2007, 44, 89.

[18] Huang, Y.-E.; Gard, G.-L.; Shreeve, J.-M. Tetrahedron Lett. 2010, 51, 6951.

[19] Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905.

[20] Oladeinde, O. A.; Hong, S. Y.; Holland, R. J.; Maciag, A. E.; Keefer, L. K.; Saavedra, J. E.; Nandurdikar, R. S. Org. Lett. 2010, 12, 4256.

[21] Gaur, M.; Goel, M.; Sridhar, L.; Ashok, T. D. S.; Prabhakar, S.; Dureja, P.; Raghunathan, P.; Eswaran, S. V. Monatsh. Chem. 2012, 143, 283.

[22] Huigens, R. W.; Rogers, S. A.; Steinhauer, A. T.; Melander, C. Org. Biomol. Chem. 2009, 7, 794.

[23] Karuturi, R.; Al-Horani, R. A.; Mehta, S. C.; Gailani, D.; Desai, U. R. J. Med. Chem. 2013, 56, 2415.

[24] Jurášeka, M.; D?ubákb, P.; Sedlákc, D.; Dvo?ákováa, H.; Hajdúchb, M.; Bart?někc, P.; Drašar, P. Steroids 2013, 78, 356.

[25] Camp, C.; Dorbes, S.; Picard, C.; Benoist, E. Tetrahedron Lett. 2008, 49, 1979.

[26] Hung, H.-C.; Cheng, C.-W.; Ho, I.-T.; Chung, W.-S. Tetrahedron Lett. 2009, 50, 302.

[27] Hung, H.-C.; Cheng, C.-W.; Wang, Y.-Y.; Chen, Y.-J.; Chung, W.-S. Eur. J. Org. Chem. 2009, 6360.

[28] Huang, H.-J.; Fang, H.-Y.; Chir, J.-L.; Wu, A.-T. Luminescence 2011, 26, 518.

[29] Li, C.; Tang, J.; Xie, J. Tetrahedron 2009, 65, 7935.

[30] Romero, T.; Orenes, R. A.; Tárraga, A.; Molina, P. Organo-metallics 2013, 32, 5740.

[31] Wei, P.-F.; Yan, X.-Z.; Li, J.-Y.; Ma, Y.-J.; Yao, Y.; Huang, F.-H. Tetrahedron 2012, 68, 9179.

[32] Ol'shevskaya, V. A.; Makarenkov, A. V.; Kononova, E. G.; Petrovskii, P. V.; Verbitskiy, E. V.; Rusinov, G. L.; Charushin, V. N.; Hey-Hawkins, E.; Kalinin, V. N. Polyhedron 2012, 42, 302.

[33] Zhang, X. J.; Li, H. Y.; You, L. F.; Tang, Y.; Hsung, R. P. Adv. Synth. Catal. 2006, 348, 2437.

[34] Sarmiento-Sánchez, J. I.; Ochoa-Teran, A.; Rivero, I. A. ARKIVOC 2011, 177.

[35] Scott, S. O.; Gavey, E. L.; Lind, S. J.; Gordon, K. C.; Crowley, J. D. Dalton Trans. 2011, 40, 12117.

[36] Guisado-Barrios, G.; Bouffard, J.; Donnadieu, B.; Bertrand, G. Organometallics 2011, 30, 6017.

[37] Schweinfurth, D.; Büttner, N.; Hohloch, S.; Deibel, N.; Klein, J.; Sarkar, B. Organometallics 2013, 32, 5834.

[38] Singh, N.; Metla, B. P. R.; Elias, A. J. J. Organomet. Chem. 2012, 717, 99.

[39] Li, Y.-J.; Huffman, J. C.; Flood, A. H. Chem. Commun. 2007, 2692.

[40] Fletcher, J. T.; Bumgarner, B. J.; Engels, N. D.; Skoglund, D. A. Organometallics 2008, 27, 5430.

[41] Mulla, K.; Shaik, H.; Thompson, D. W.; Zhao, Y. M. Org. Lett. 2013, 15, 4532.

[42] Li, C.; Henry, E.; Mani, N. K.; Tang, J.; Brochon, J. C.; Deprez, E.; Xie, J. Eur. J. Org. Chem. 2010, 2395.

[43] Ruan, Y.-B.; Yu, Y.-H.; Li, C.; Bogliotti, N.; Tang, J.; Xie, J. Tetrahedron 2013, 69, 4603.

[44] Brombosz, S. M.; Appleton, A. L.; Zappas, A. J.; Bunz, U. H. F. Chem. Commun. 2010, 46, 1419.

[45] Shi, W.-J.; Liu, J.-Y.; Ng, D. K. P. Chem. Asian J. 2012, 7, 196.

[46] Zhou, M.-Z.; Zhang, X.; Bai, M.-F.; Shen, D.-W.; Xu, B.-G.; Kao, J.; Ge, X.; Achilefu, X. RSC Adv. 2013, 3, 6756.

[47] Wei, J.-J.; Jin, L.; Wan, K.; Zhou, C.-H. Bull. Korean Chem. Soc. 2011, 32, 229.

[48] Lau, Y. H.; Rutledge, P. J.; Watkinson, M.; Todd, M. H. Chem. Soc. Rev. 2011, 40, 2848.

[49] Hemamalinia, A.; Das, T. M. New J. Chem. 2013, 37, 2419.

[50] Xu, H.-R.; Li, K.; Liu, Q.; Wu, T.-M.; Wang, M.-Q.; Hou, J.-T.; Huang, Z.; Xie, Y.-M.; Yu, X.-Q. Analyst 2013, 2329.

[51] White, N. G.; Beer, P. D. Org. Biomol. Chem. 2013, 11, 1326.

[52] Mohammed, A. I.; Abboud, Z. H.; Alghanimi, A. H. O. Tetrahedron Lett. 2012, 53, 5081.

[53] Mekni, N.; Baklouti, A. J. Soc. Chim. Tunisie 2009, 11, 15.

[54] Jervis, P. J.; Moulis, M.; Jukes, J. P.; Ghadbane, H.; Cox, L. R.; Cerundolo, V.; Besra, G. S. Carbohydr. Res. 2012, 356, 152.

[55] Bedard, A.-C.; Collins, S. K. J. Am. Chem. Soc. 2011, 133, 19976.

[56] Damodiran, M.; Muralidharan, D.; Perumal, P. T. Bioorg. Med. Chem. Lett. 2009, 19, 3611.

[57] Lal, K.; Kumar, A.; Pavan, M. S.; Kaushik, C. P. Bioorg. Med. Chem. Lett. 2012, 22, 4353.

[58] Singh, M. K.; Tilak, R.; Nath, G.; Awasthi, S. K.; Agarwal, A. Eur. J. Med. Chem. 2013, 63, 635.

[59] Skarpos, H.; Osipov, S. N.; Vorob'eva, D. V.; Odinets, I. L.; Lork, E.; Roeschenthaler, G.-V. Org. Biomol. Chem. 2007, 5, 2361.

[60] Pereira, G. R.; Santos, L. J.; Luduvico, I.; Alves, R. B.; de Freitas, R. P. Tetrahedron Lett. 2010, 51, 1022.

[61] Rajesh, R.; Periyasami, G.; Raghunathan, R. Tetrahedron Lett. 2010, 51, 1896.

[62] Megiatto, J. D.; Schuster, D. I. J. Am. Chem. Soc. 2008, 130, 12872.

[63] Mames, I.; Wawrzyniak, U. E.; Wo?ny, M.; Bilewicz, R.; Korybut-Daszkiewicz, B. Dalton Trans. 2013, 42, 2382.

[64] Mekni, N. H.; Baklouti, A. Heterocycles 2012, 85, 1727.

[65] Yoshida, Y.; Takizawa, S.; Sasai, H. Tetrahedron Lett. 2011, 52, 6877.

[66] Lin, H. N. Walsh, C. T. J. Am. Chem. Soc. 2004, 126, 13998.

[67] Krim, J.; Taourirte, M.; Engels, J. W. Molecules 2012, 17, 179.

[68] Huo, J.-P.; Lv, M.-X.; Wang, Z.-Y.; Li, Y.-Z. Chin. J. Chem. 2012, 30, 2411.

[69] Mao, C.-X.; Wang, Z.-Y.; Tan, Y.-H.; Xue, F.-L. Chin. J. Org. Chem. 2011, 31, 1377 (in Chinese).

(毛超旭, 汪朝阳, 谭越河, 薛福玲, 有机化学, 2011, 31, 1377.)

[70] Mo, Y.-Q.; Wang, Z.-Y.; Mei, W.-J.; Fu, J.-H.; Tan, Y.-H.; Luo, S.-H. Monatsh. Chem. 2012, 143, 443.

[71] Luo, S.-H.; Wang, Q.-F.; Wang, Z.-Y.; Peng P. Res. Chem. Intermed. 2013, 39, 2513.

[72] Tan, Y.-H.; Li, J.-X.; Xue, F.-L.; Qi. J.; Wang, Z.-Y. Tetrahedron 2012, 68, 2827.

[73] Huo, J. P.; Luo, J. C.; Wu, W.; Xiong, J. F.; Mo, G. Z.; Wang, Z. Y. Ind. Eng. Chem. Res. 2013, 52, 11850.

[74] Kumar, K.; Sagar, S.; Esau, L.; Kaur, M.; Kumar, V. Eur. J. Med. Chem. 2012, 58, 153.

[75] Kumar, K.; Carrere-Kremer, S.; Kremer, L.; Guerardel, Y.; Biot, C.; Kumar, V. Dalton Trans. 2013, 42, 1492.

[76] Midya, G. C.; Paladhi, S.; Bhowmik, S.; Saha, S.; Dash, J. Org. Biomol. Chem. 2013, 11, 3057.

[77] Elamari, H.; Jlalia, I.; Louet, C.; Herscovici, J.; Meganem, F.; Girard, C. Tetrahedron: Asymmetry 2010, 21, 1179.

[78] Elamari, H.; Meganem, F.; Herscovici, J.; Girard, C. Tetrahedron Lett. 2011, 52, 658.

[79] Elamari, H.; Slimi, R.; Chabot, G. G.; Quentin, L.; Scherman, D.; Girard, C. Eur. J. Med. Chem. 2013, 60, 360.

[80] Isaacman, M. J.; Corigliano, E. M.; Theogarajan, L. S. Biomacro- molecules 2013, 14, 2996.

[81] Zhou, Q. H.; Gui, J. H.; Pan, C.-M.; Albone, E.; Cheng, X.; Suh, E. M.; Grasso, L.; Ishihara, Y.; Baran, P. S. J. Am. Chem. Soc. 2013, 135, 12994.

[82] Sapsford, K. E.; Algar, W. R.; Berti, L.; Gemmill, K. B.; Casey, B. J.; Oh, E.; Stewart, M. H.; Medintz, I. L. Chem. Rev. 2013, 113, 1904.

[83] Beal, D. M.; Albrow, V. E.; Burslem, G.; Hitchen, L.; Fernandes, C.; Lapthorn, C.; Roberts, L. R.; Selby, M. D.; Jones, L. H. Org. Biomol. Chem. 2012, 10, 548.

[84] Aucagne, V.; Leigh, D. A. Org. Lett. 2006, 8, 4505.

[85] Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A.; Capuzzolo, F. Tetrahedron 2009, 65, 10573.

[86] Aizpurua, J. M.; Azcune, I.; Fratila, R. M.; Balentova, E.; Sagartzazu-Aizpurua, M.; Miranda, J. I. Org. Lett. 2010, 12, 1584.

[87] Doak, B. C.; Scanlon, M. J.; Simpson, J. S. Org. Lett. 2011, 13, 537.

[88] Kamal, A.; Shankaraiah, N.; Reddy. C. R.; Prabhakar, S.; Markandeya, N.; Srivastava, H. K.; Sastry, G. N. Tetrahedron 2010, 66, 5498.

[89] Kovalovs, A.; Novosjolova, I.; Bizdena, E.; Bizane, I.; Skardziute, L.; Kazlauskas, K.; Jursenas, S.; Turks, M. Tetrahedron Lett. 2013, 54, 850.

[90] Potewar, T. M.; Petrova, K. T.; Barros, M. T. Carbohydr. Res. 2013, 79, 60.

[91] Westermann, B.; Dörner, S.; Brauch, S.; Schaks, A.; Heinke, R.; Stark, S.; van Delft, F. L.; van Berkel, S. S. Carbohydr. Res. 2013, 371, 61.

[92] Yuan, Z; Kuang, G.-C.; Clark, R. J.; Zhu, L. Org. Lett. 2012, 14, 2590.

[93] Guiard, J.; Fiege, B.; Kitov, P. I.; Peters, T.; Bundle, D. R. Chem. Eur. J. 2011, 17, 7438.

[94] Wang, Z.-Y.; Tan Y.-H.; Huo, J.-P.; Qi, J.; Li, D. In 12th International Symposium for Chinese Organic Chemists, Eds.: Zhai, H.-B.; Wang, W., Lanzhou University, Lanzhou, 2012, pp. 27.

[95] Banday, A. H.; Arora, B. S.; Alam, M. S.; Kumar, H. M. S. Helv. Chim. Acta 2007, 90, 2368.

[96] Arora, B. S.; Shafi, S.; Singh, S.; Ismail, T.; Kumar, H. M. S. Carbohydr. Res. 2008, 343, 139.

[97] Yan, W.-M.; Wang, Q.-Y.; Chen, Y.-F.; Petersen, J. L.; Shi, X.-D. Org. Lett. 2010, 12, 3308.

双-1,2,3-三唑化合物的合成与应用研究进展

Progresses in Syntheses and Applications of Bis-1,2,3-triazoles

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