Reviews

Recent Advances in the Synthesis and Application of Tetrazoles

  • Dai Lingling ,
  • Cui Shengfeng ,
  • Damu Guri L. V. ,
  • Zhou Chenghe
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  • 1 School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715;
    2 Postdoctoral fellow from Indian Institute of Chemical Technology (IICT), Hyderabad-500 607, India

Received date: 2012-08-31

  Revised date: 2012-11-05

  Online published: 2012-11-14

Supported by

Project supported by the National Natural Science Foundation of China (No. 21172181), the Research Fellowship for International Young Scientists from International (Regional) Cooperation and Exchange Program (No. 81250110089), the Key Program from Natural Science Foundation of Chongqing City (No. CSTC2012jjB10026), the Specialized Research Fund for the Doctoral Program of Higher Education of China (No. SRFDP 20110182110007) and the Fundamental Research Funds for the Central Universities (Nos. XDJK2011D007, XDJK2012B026).

Abstract

Tetrazole is an important five-membered aromatic heterocycle with poly-nitrogen electron-rich planar structural feature. This unique structure endows tetrazole derivatives as drugs, explosives, functional materials etc. to exhibit wide potential applications in medicinal, agrochemical, material science and so on. Relevant researches have been becoming active and some important achievements have been made. Based our work on azoles and referring to other literature in recent 5 years, this review systematically summarized the recent advances in the synthesis of tetrazole compounds and their application researches as medicinal drugs, agrochemicals and materials.

Cite this article

Dai Lingling , Cui Shengfeng , Damu Guri L. V. , Zhou Chenghe . Recent Advances in the Synthesis and Application of Tetrazoles[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 224 -244 . DOI: 10.6023/cjoc201208036

References

[1] Cui, S.-F.; Wang, Y.; Lv, J.-S.; Damu, G. L. V.; Zhou, C.-H. Sci. Sin. Chim. 2012, 42, 110 (in Chinese). (崔胜峰, 王艳, 吕敬松, Guri L. V. Damu, 周成合, 中国科学:化学, 2012, 42, 1105.)
[2] Cui, S.-F.; Zhou, C.-H.; Geng, R.-X.; Ji, Q.-G. Chin. J. Biochem. Pharm. 2012, 33, 311 (in Chinese). (崔胜峰, 周成合, 耿蓉霞, 吉庆刚, 中国生化药物杂志, 2012, 33, 311.)
[3] Zhang, H.-Z.; Ji, Q.-G.; Geng, R.-X.; Zhou, C.-H. Chin. J. Org. Chem. 2012, 31, 1963 (in Chinese). (张慧珍, 吉庆刚, 耿蓉霞, 周成合, 有机化学, 2012, 31, 1963.)
[4] Wu, J.; Panek, J. S. Angew. Chem., Int. Ed. 2010, 122, 6301.
[5] Zhang, F.-F.; Gan, L.-L.; Zhou, C.-H. Bioorg. Med. Chem. Lett. 2010, 20, 1881.
[6] Zhang, F.-F.; Zhou, C.-H.; Yan, J.-P. Chin. J. Org. Chem. 2010, 30, 783 (in Chinese). (张飞飞, 周成合, 颜建平, 有机化学, 2010, 30, 783.)
[7] Zhang, Y.-Y.; Zhou, C.-H. Bioorg. Med. Chem. Lett. 2011, 21, 4349.
[8] Wu, J.; Mi, J.-L.; Zhou, C.-H. Chin. Pharm. J. 2007, 42, 404 (in Chinese). (吴俊, 米佳丽, 周成合, 中国药学杂志, 2007, 42, 404.)
[9] Cai, J.-L.; Li, S.; Zhou, C.-H.; Gan, L.-L.; Wu, J. Chin. J. New Drugs 2009, 18, 598 (in Chinese). (蔡佳利, 李硕, 周成合, 甘淋玲, 吴俊, 中国新药杂志, 2009, 18, 598.)
[10] Fang, B.; Zhou, C.-H.; Rao, X.-C. Eur. J. Med. Chem. 2010, 45, 4388.
[11] Zhang, S.-L.; Damu, G. L. V.; Zhang, L.; Geng, R.-X.; Zhou, C.-H. Eur. J. Med. Chem. 2012, 55, 164.
[12] Meng, J.-P.; Geng, R.-X.; Zhou, C.-H.; Gan, L.-L.; Wu, J. Chin. J. New Drugs 2009, 16, 1505 (in Chinese). (孟江平, 耿蓉霞, 周成合, 甘淋玲, 吴俊, 中国新药杂志, 2009, 16, 1505.)
[13] Wang, Y.; Zhou, C.-H. Sci. Sin. Chim. 2011, 41, 1429 (in Chinese). (王艳, 周成合, 中国科学: 化学, 2011, 41, 1429.)
[14] Zhou, C.-H.; Wang, Y. Curr. Med. Chem. 2012, 19, 239.
[15] Wang, X.-L.; Wan, K.; Zhou, C.-H. Eur. J. Med. Chem. 2010, 45, 4631.
[16] Shi, Y.; Zhou, C.-H.; Zhou, X.-D.; Geng, R.-X.; Ji, Q.-G. Acta Pharm. Sin. 2011, 46, 798 (in Chinese). (时园, 周成合, 周向东, 耿蓉霞, 吉庆刚, 药学学报, 2011, 46, 798.)
[17] Shi, Y.; Zhou, C.-H. Bioorg. Med. Chem. Lett. 2011, 21, 956.
[18] Zhang, Y.-Y.; Mi, J.-L.; Zhou, C.-H.; Zhou, X.-D. Eur. J. Med. Chem. 2011, 46, 4391.
[19] Wang, Y.; Damu, G. L. V.; Lv, J.-S. Geng, R.-X.; Yang, D.-C.; Zhou, C.-H. Bioorg. Med. Chem. Lett. 2012, 21, 5363.
[20] Wang, X.-L.; Gan, L.-L.; Yan, C.-Y.; Zhou, C.-H. Sci. Sin. Chim. 2011, 41, 451 (in Chinese). (王宪龙, 甘淋玲, 闫聪彦, 周成合, 中国科学: 化学, 2011, 41, 451.)
[21] Rajasekaran, A.; Murugesan, S.; Kalasalingam, A. R. Arch. Pharm. Res. 2006, 29, 535.
[22] Kamble, R. R.; Biradar, D. B.; Meti, G. Y.; Taj, T.; Gireesh, T.; Khazi, I. A. M.; Vaidyanathan, S. T.; Mohandoss, R.; Sridhar, B.; Parthasarathi, V. J. Chem. Sci. 2011, 123, 393.
[23] Gutmann, B.; Roduit, J. P.; Dominique, R.; Kappe, C. O. Angew. Chem., Int. Ed. 2010, 49, 7101.
[24] Sureshbabu, V. V.; Nagendra, N.; Nagendra. G. J. Org. Chem. 2009, 74, 153.
[25] El Kaim, L.; Grimaud, L.; Patil, P. Org. Lett. 2011, 13, 1261.
[26] Saha, B.; Sharma, S.; Sawant, D.; Kundu, B. Tetrahedron 2008, 64, 8676.
[27] Wei, J.-J.; Wang, Y.; Wang, X.-L.; Zhou, C.-H.; Ji, Q.-G. Chin. Pharm. J. 2011, 46, 481 (in Chinese). (魏金建, 王艳, 王宪龙, 周成合, 吉庆刚, 中国药学杂志, 2011, 46, 481.)
[28] Jin, T.; Kitahara, F.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 2824.
[29] Aridoss, G.; Laali, K. K. Eur. J. Org. Chem. 2011, 31, 6343.
[30] Huang, J.-J.; He, X.-P.; Dong, Q.; Hu, J.; Shi, X.-X. Chin. J. Synth. Chem. 2010, 18, 64 (in Chinese). (黄家吉, 贺晓鹏, 董菁, 胡键, 施小新, 合成化学, 2010, 18, 64.)
[31] Manche?o, O. G.; Bolm, C. Org. Lett. 2007, 9, 2591.
[32] Nasrollahzadeh, M.; Bayat, Y.; Habibi, D.; Moshaee, S. Tetrahedron Lett. 2009, 50, 4435.
[33] Qi, G.; Dai, Y. Chin. Chem. Lett. 2010, 21, 1029.
[34] Gowd, M. R. M. B.; Pasha, M. A. J. Chem. Sci. 2011, 123, 75.
[35] Teimouri, A.; Chermahini, A. N. Polyhedron 2011, 30, 2606.
[36] Lasri, J.; Rodríguez, M. J. F.; Guedes da Silva, M. F. C.; Smoleński, P.; Kopylovich, M. N.; Fraústo da Silva, J. J. R.; Pombeiro, A. J. L. J. Organomet. Chem. 2011, 696, 3513.
[37] Khamooshi, F.; Modarresi-Alam, A. R. Chin. Chem. Lett. 2010, 21, 892.
[38] Nasrollahzadeh, M.; Habibi, D.; Shahkarami, Z.; Bayat, Y. Tetrahedron 2009, 65, 10715.
[39] Wang, G.-X.; Sun, B.-P.; Peng, C.-H. Org. Process Res. Dev. 2011, 15, 986.
[40] Sun, H.-B.; Chen, W.-L.; Sun, Y.-H.; Qin, P.; Qi, X. Adv. Mater. Res. 2012, 396398, 2416.
[41] Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, M. D. Tetrahedron 2008, 64, 1430.
[42] Dighe, S. N.; Jain, K. S.; Srinivasan, K. V. Tetrahedron Lett. 2009, 50, 6139.
[43] Habibi, D.; Nasrollahzadeha, M.; Kamali, T. A. Green Chem. 2011, 13, 3499.
[44] Polivanova, A. G.; Shkavrov, S. V.; Churakov, A. V.; Lermontov, A. S.; Lermontov, S. A. Tetrahedron Lett. 2010, 51, 4205.
[45] Webster, S. P.; Binniea, M.; McConnell, K. M. M.; Sooy, K.; Ward, P.; Greaney, M. F.; Vinter, A.; Pallin, T. D.; Dyke, H. J.; Gill, M. I. A.; Warner, I.; Seckl, J. R.; Walker, B. R. Bioorg. Med. Chem. Lett. 2010, 20, 3265.
[46] Li, J.; Stephanie, Y.; Tao, S.-Y.; Wang, H.-X.; Li, J. J.; Swartz, S.; Musial, C.; Hernandez, A. A.; Flynn, N.; Murphy, B. J.; Beehler, B.; Dickinson, K. E.; Giupponi, L.; Grover, G.; Seethala, R.; Sleph, P.; Slusarchyk, D.; Yan, M.-J.; Humphreys, W. G.; Zhang, H.-J.; Ewing, W. R.; Robl, J. A.; Gordon, D.; Tino, J. A. Bioorg. Med. Chem. Lett. 2008, 18, 1825.
[47] El Kaim, L.; Grimaud, L.; Patil, P. Org. Lett. 2011, 13, 1261.
[48] Saha, B.; Sharma, S.; Sawant, D.; Kundu, B. Tetrahedron 2008, 64, 8676.
[49] Polivanova, A. G.; Shkavrov, S. V.; Churakov, A. V.; Lermontov, A. S.; Lermontov, S. A. Tetrahedron Lett. 2010, 51, 4205.
[50] Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, M. D. Tetrahedron 2008, 64, 1430.
[51] Wu, T.-Z.; Liu, X.-H.; Zhang, F.-L.; Xie, M.-H. Acta Pharm. Sin. 2006, 41, 537 (in Chinese). (吴泰志, 刘晓华, 张福利, 谢美华, 药学学报, 2006, 41, 537.)
[52] Zhou, C.-H.; Zhang, F.-F.; Gan, L.-L.; Zhang, Y.-Y.; Geng, R.-X. Sci. China, Ser. B: Chem. 2009, 39, 208 (in Chinese) (周成合, 张飞飞, 甘淋玲, 张奕奕, 耿蓉霞, 中国科学B辑: 化学, 2009, 39, 208.)
[53] Zhou, C.-H.; Gan, L.-L.; Zhang, Y.-Y.; Zhang, F.-F.; Wang, G.-Z.; Jin, L.; Geng, R.-X. Sci. China, Ser. B: Chem. 2009, 52, 415.
[54] Zhou, C.-H.; Zhang, Y.-Y.; Yan, C.-Y.; Wan, K.; Gan, L.-L.; Shi, Y. Anti-Cancer Agents Med. Chem. 2010, 10, 371.
[55] Chang, J.-J.; Wang, Y.; Zhang, H.-Z.; Zhou, C.-H.; Geng, R.-X.; Ji, Q.-G. Chem. J. Chin. Univ. 2011, 32, 1970 (in Chinese). (常娟娟, 王艳, 张慧珍, 周成合, 耿蓉霞, 吉庆刚, 高等学校化学学报, 2011, 32, 1970.)
[56] Chawla, G.; Bansal, A. K. Eur. J. Pharm. Sci. 2007, 32, 45.
[57] Hirlekar, R. S.; Sonawane, S. N.; Kadam, V. J. AAPS PharmSciTec h 2009, 10, 858.
[58] Wu, J.-H.; Wang, Q.-J.; Guo, J.-Y.; Hu, Z.-Y.; Yin, Z.-Y.; Xu, J.-Y.; Wu, X.-M. Eur. J. Pharmacol. 2008, 589, 220.
[59] Arhancet, G. B.; Woodard, S. S.; Iyanar, K.; Case, B. L.; Woerndle, R.; Dietz, J. D.; Garland, D. J.; Collins, J. T.; Payne, M. A.; Blinn, J. R.; Pomposiello, S. I.; Hu, X.; Heron, M. I.; Huang, H.-C.; Lee, L. F. J. Med. Chem. 2010, 53, 5970.
[60] Gagnon, A.; Landry, S.; Coulombe, R.; Jakalian, A.; Guse, I.; Thavonekham, B.; Bonneau, P. R.; Yoakim, C.; Simoneau, B. Bioorg. Med. Chem. Lett. 2009, 19, 1199.
[61] Muraglia, E.; Kinzel, O. D.; Laufer, R.; Miller, M. D.; Moyer, G.; Munshi, V.; Orvieto, F.; Palumbi, M. C.; Pescatore, G.; Rowley, M.; Williams, P. D.; Summa, V. Bioorg. Med. Chem. Lett. 2006, 16, 2748.
[62] O'Meara, J. A.; Jakalian, A.; LaPlante, S.; Bonneau, P. R.; Coulombe, R.; Faucher, A. M.; Guse, I.; Landry, S.; Racine, J.; Simoneau, B.; Thavonekham, B.; Yoakim, C. Bioorg. Med. Chem. Lett. 2007, 17, 3362.
[63] Zhan, P.; Liu, H.-B.; Liu, X.-Y.; Wang, Y.; Pannecouque, C.; Witvrouw, M.; De Clercq, E. Med. Chem. Res. 2010, 19, 652.
[64] Crosby, D. C.; Lei, X.-Y.; Gibbs, C. G.; McDougall, B. R.; Robinson, W. E.; Reinecke, M. G. J. Med. Chem. 2010, 53, 8161.
[65] Bosch, L.; Delelis, O.; Subra, F.; Deprez, E.; Witvrow, M.; Vilarrasa, J. Tetrahedron Lett. 2012, 53, 514.
[66] Yan, S.-Q.; Larson, G.; Wu, J. Z.; Appleby, T.; Ding, Y.-L.; Hamatake, R.; Hong, Z.; Yao, N. Bioorg. Med. Chem. Lett. 2007, 17, 63.
[67] Ronn, R.; Gossas, T.; Sabnis, Y. A.; Daoud, H.; Aakerblom, E.; Danielson, U. H.; Sandstrom, A. Bioorg. Med. Chem. 2007, 15, 4057.
[68] Zarubaev, V. V.; Golod, E. L.; Anfimov, P. M.; Shtro, A. A.; Saraev, V. V.; Gavrilov, A. S.; Logvinov, A. V.; Kiselev, O. I. Bioorg. Med. Chem. 2010, 18, 839.
[69] Anacona, J. R.; Osorio, I. Transition Met. Chem. 2008, 33, 517.
[70] Pochini, L.; Galluccio, M.; Scumaci, D.; Giangregorio, N.; Tonazzi, A.; Palmieri, F.; Indiveri, C. Chem. Biol. Interact. 2008, 173, 187.
[71] Lee, C.-H.; Liu, J.-W.; Li, C.-C.; Chien, C.-C.; Tang, Y.-F.; Su, L.-H. Antimicrob. Agents Chemother. 2011, 55, 4058.
[72] Yildirir, Y.; Us, M. F.; Colak, N.; Ozkan, H.; Yavuz, S.; Disli, A.; Ozturk, S.; Turker, L. Med. Chem. Res. 2009, 18, 91.
[73] Shreaz, S.; Wani, M. Y.; Ahmad, S. R.; Ahmad, S. I.; Bhatia, R.; Athar, F.; Nikhat, M.; Khan, L. A. Eur. J. Med. Chem. 2012, 48, 363.
[74] Diwakar, S. D.; Bhagwat, S. S.; Shingare, M. S.; Gill, C. H. Bioorg. Med. Chem. Lett. 2008, 18, 4678.
[75] El-Sayed, W. A.; Abdel Megeid, R. E.; Abbas, H.-A. S. Arch. Pharm. Res. 2011, 34, 1085.
[76] Navidpour, L.; Amini, M.; Shafaroodi, H.; Abdi, K.; Ghahremani, M. H.; Dehpourd, A. R.; Shafiee, A. Bioorg. Med. Chem. Lett. 2006, 16, 4483.
[77] Al-Hourani, B. J.; Sharma, S. K.; Mane, J. Y.; Tuszynski, J.; Baracos, V.; Kniess, T.; Suresh, M.; Pietzsch, J.; Wuest, F. Bioorg. Med. Chem. Lett. 2011, 21, 1823.
[78] Kuduk, S. D.; Chang, R. K.; DiPardo, R. M.; Di Marco, C. N.; Murphy, K. L.; Ransom, R. W.; Reiss, D. R.; Tang, C.; Prueksaritanon, T.; Pettibone, D. J.; Bock, M. G. Bioorg. Med. Chem. Lett. 2008, 18, 5107.
[79] Trécant, C.; Dlubala, A.; George, P.; Pichat, P.; Ripoche, I.; Troin, Y. Eur. J. Med. Chem. 2011, 46, 4035.
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