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2018 , Vol. 38 >Issue 5: 1052 - 1064

DOI: https://doi.org/10.6023/cjoc201710018

综述与进展

N2-取代1,2,3-三唑的合成研究进展

  • 朱莉莉 ,
  • 张辉 ,
  • 王春杰 ,
  • 陈自立
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  • a 周口师范学院化学化工学院 周口 466001;
    b 中国人民大学化学系 北京 100872

收稿日期: 2017-12-16

  修回日期: 2017-12-20

  网络出版日期: 2018-01-10

基金资助

国家自然科学基金（No.21472237）、河南省科技计划项目（No.162300410197）、周口师范学院科研创新基金（No.ZKNUA201701）和周口师范学院科研启动基金（No.ZKNUB2013001）资助项目.

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Recent Progress in the Synthesis of N2-Substituted 1, 2, 3-Triazoles

  • Zhu Lili ,
  • Zhang Hui ,
  • Wang Chunjie ,
  • Chen Zili
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  • a School of Chemistry and Chemical Engneering, Zhoukou Normal University, Zhoukou 466001;
    b Department of Chemistry, Renmin University of China, Beijing 100872

Received date: 2017-12-16

  Revised date: 2017-12-20

  Online published: 2018-01-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 21472237), the Science and Technology Research Program of Henan Province (No. 162300410197), the Scientific Research Innovation Foundation of Zhoukou Normal University (No. ZKNUA201701) and the Doctoral Scientific Research Foundation of Zhoukou Normal University (No. ZKNUB2013001).

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摘要

N-取代1，2，3-三唑化合物在有机合成、药物化学和材料科学等领域具有广泛的应用价值.其中N1-取代1，2，3-三唑化合物的合成方法已经非常成熟，而N2-取代1，2，3-三唑的合成报道相对较少.在现有研究报道中，主要通过1，2，3-三唑的选择性官能化及双芳腙或偶氮苯的氧化环化两类方法得到.结合我们课题组的研究工作，综述了2000年以来N2-烷基、烯丙基、炔丙基、烯基、芳基取代1，2，3-三唑的合成方法进展.

关键词： 1,2,3-三唑; 选择性N2-官能化; 烷基化; 烯丙基化; 炔丙基化; 烯基化; 芳基化; 环化

本文引用格式

朱莉莉 , 张辉 , 王春杰 , 陈自立 . N2-取代1,2,3-三唑的合成研究进展[J]. 有机化学, 2018 , 38(5) : 1052 -1064 . DOI: 10.6023/cjoc201710018

Abstract

N-Substituted 1, 2, 3-triazole is an important structural unit in organic chemistry, and has widely utilized in organic synthesis, medicinal chemistry and material science. The chemistry of N1-substituted 1, 2, 3-triazoles has attracted much attention from organic chemists, while the synthesis and application of their N2-isomers have been far less explored. The recent progress on the research field of N2-alkyl, allyl, propargyl, vinyl, aryl substituted 1, 2, 3-triazoles since year 2000 is summarized, including some research of our group. The content is classified by different synthetic methods, such as selective functionalization of 1, 2, 3-triazoles and oxidative cyclization of bisarylhydrazones or azobenzenes.

Key words： 1, 2, 3-triazole; selective N2-fuctionalization; alkylation; allylation; propargylation; vinylation; arylation; cyclization

参考文献

[1] (a) Jewetta, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272.
(b) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905.
(c) Katritzky, A. R.; Rachwal, S. Chem. Rev. 2010, 110, 1564.
(d) Wang, D.; Gautam, L. N. S.; Bollinger, C.; Harris, A.; Li, M.; Shi, X. Org. Lett. 2011, 13, 2618.
(e) Huang, J.; Zhou, H.; Chen, Z. Chin. J. Org. Chem. 2016, 36, 1555(in Chinese). (黄家翩, 周豪, 陈知远, 有机化学, 2016, 36, 1555.)
(f) Chen, Y.; Zheng, C.; Peng, X.; Fu, Q.; Wu, L.; Lin, Q. Chin. J. Org. Chem. 2016, 36, 1779(in Chinese). (陈昱学, 郑超, 彭潇楚, 符清坛, 吴禄勇, 林强, 有机化学, 2016, 36, 1779.)
(g) Gavlik, K. D.; Lesogorova, S. G.; Sukhorukova, E. S.; Subbotina, J. O.; Slepukhin, P. A.; Benassi, E.; Belskaya, N. P. Eur. J. Org. Chem. 2016, 2700.
[2] (a) Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565.
(b) Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry, Ed.:Padwa, A., Wiley, New York, 1984, pp. 1~176.
[3] (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
(b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
(c) Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998.
(d) Rasmussen, L. K.; Boren, B. C.; Fokin, V. V. Org. Lett. 2007, 9, 5337.
[4] (a) Ma, Z.; Lin, Y.; Cheng, Y.; Wu, W.; Cai, R.; Chen, S.; Shi, B.; Han, B.; Shi, X.; Zhou, Y.; Du, L.; Li, M. J. Med. Chem. 2016, 59, 2151.
(b) Chow, H.-F.; Lo, C.-M.; Chen, Y. Top. Heterocycl. Chem. 2012, 28, 137.
(c) El-Sagheerab, H. A.; Brown, T. Chem. Soc. Rev. 2010, 39, 1388.
(d) Xu, L.; Li, Y.; Li, Y. Asian J. Org. Chem. 2014, 3, 582.
(e) Xiao, L.; Ren, P.; Jing, X.; Ren, L.; Li, Z. Chin. J. Org. Chem. 2007, 37, 3085(in Chinese). (肖立伟, 任萍, 景学敏, 任丽磊, 李政戴, 有机化学, 2007, 37, 3085.)
(f) Teders, M. Pitzer, L.; Buss, S.; Glorius, F. ACS Catal. 2017, 7, 4053.
[5] (a) Schulze, B.; Schubert, U. S. Chem. Soc. Rev. 2014, 43, 2522.
(b) Wu, J. M.S. Thesis, Wuhan Institute of Technology, Wuhan, 2014 (in Chinese). (吴俊, 硕士论文, 武汉工程大学, 武汉, 2014.)
(c) Cai, R.; Yan, W.; Bologna, M. G.; Silva, K.; Ma, Z.; Finklea, H. O.; Petersen, J. L.; Li, M.; Shi, X. Org. Chem. Front. 2015, 2, 141.
(d) Chen, Y.; Wu, J.; Ma, S.; Zhou, S.; Meng, X.; Jia, L.; Pan, Z. J. Mol. Struct. 2015, 1089, 1.
(e) Shi, S.; Kuang, C. J. Org. Chem. 2014, 79, 6105.
(f) Lv, Y.; Zhu, L.-L.; Liu, H.; Wu, Y.; Chen, Z.; Fu, H.; Tian, Z. Anal. Chim. Acta 2014, 839, 74.
(g) Liu, H.; Ding, H.; Zhu, L.; Wang, Y.; Chen, Z.; Tian, Z. J. Fluoresc. 2015, 25, 1259.
(h) Jo, J.; Lee, H. Y.; Liu, W.; Olasz, A.; Chen, C.-H.; Lee, D. J. Am. Chem. Soc. 2012, 134, 16000.
(i) Gavlik, K. D.; Sukhorukova, E. S.; Shafran, Y. M.; Slepukhin, P. A.; Benassi, E.; Belskaya, N. P. Dyes Pigm. 2017, 136, 229.
[6] (a) Mangion, I. K.; Sherry, B. D.; Yin, J.; Fleitz, F. J. Org. Lett. 2012, 14, 3458.
(b) Adibekian, A.; Martin, B. R.; Wang, C.; Hsu, K.-L.; Bachovchin, D. A.; Niessen, S.; Hoover, H.; Cravatt, B. F. Nat. Chem. Biol. 2011, 7, 469.
(c) Cox, C. D.; Breslin, M. J.; Whitman, D. B.; Schreier, J. D.; McGaughey, G. B.; Bogusky, M. J.; Roecker, A. J.; Mercer, S. P.; Bednar, R. A.; Lemaire, W.; Bruno, J. G.; Reiss, D. R.; Harrell, C. M.; Murphy, K. L.; Garson, S. L.; Doran, S. M.; Prueksaritanont, T.; Anderson, W. B.; Tang, C.; Roller, S.; Cabalu, T. D.; Cui, D.; Hartman, G. D.; Young, S. D.; Koblan, K. S.; Winrow, C. J.; Renger, J. J.; Coleman, P. J. J. Med. Chem. 2010, 53, 5320.
(d) Baxter, C. A.; Cleator, E.; Brands, K. M. J.; Edwards, J. S.; Reamer, R. A.; Sheen, F. J.; Stewart, G. W.; Strotman, N. A.; Wallace, D. Org. Process Res. Dev. 2011, 15, 367.
[7] Chen, Y.; Liu, Y.; Petersena, J. L.; Shi, X. Chem. Commun. 2008, 3254.
[8] Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171.
[9] Wang, X.-J.; Sidhu, K.; Zhang, L.; Campbell, S.; Haddad, N.; Reeves, D. C.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2009, 11, 5490.
[10] Wang, X.-J.; Zhang, L.; Krishnamurthy, D.; Senanayake, C. H.; Wipf, P. Org. Lett. 2010, 12, 4632.
[11] Yan, W.; Liao, T.; Tuguldur, O.; Zhong, C.; Petersen, J. L.; Shi, X. Chem.-Asian J. 2011, 6, 2720.
[12] Girish, Y. R.; Kumar, K. S. S.; Muddegowda, U.; Lokanath, N. K.; Rangappa, K. S.; Shashikanth, S. RSC Adv. 2014, 4, 55800.
[13] Shi, J.; Zhu, L.; Wen, J.; Chen, Z. Chin. J. Catal. 2016, 37, 1222.
[14] Jiang, Y.; Wang, Q.; Sun, R.; Tang, X.-Y.; Shi, M. Org. Chem. Front. 2016, 3, 744.
[15] Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem., Int. Ed. 2012, 51, 10938.
[16] Zhu, L.-L.; Xu, X.-Q.; Shi, J.-W.; Chen, B.-L.; Chen, Z. J. Org. Chem. 2016, 81, 3568.
[17] Wei, H.; Hu, Q.; Ma, Y.; Wei, L.; Liu, J.; Shi, M.; Wang, F. Asian J. Org. Chem. 2017, 6, 662.
[18] Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786.
[19] Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Org. Chem. 2004, 69, 2386.
[20] Xu, K.; Thieme, N.; Breit, B. Angew. Chem., Int. Ed. 2014, 53, 7268.
[21] Yan, Wu.; Wang, Q.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2010, 12, 3308.
[22] Duan, H.; Yan, W.; Sengupta, S.; Shi, X. Bioorg. Med. Chem. Lett. 2009, 19, 3899.
[23] Yan, W.; Ye, X.; Weise, K.; Petersen, J. L.; and Shi, X. Chem. Commun. 2012, 48, 3521.
[24] Zhang, Z.; Chang, L.; Wang, S.; Wang, H.; Yao, Z.-J. RSC Adv. 2013, 3, 18446.
[25] Poznański, J.; Najda, A.; Bretner, M.; Shugar, D. J. Phys. Chem. A 2007, 111, 6501.
[26] Kitamura, T.; Morshed, M. H.; Tsukada, S.; Miyazaki, Y.; Iguchi, N.; Inoue, D. J. Org. Chem. 2011, 76, 8117.
[27] Liu, Y.; Yan, W.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 5389.
[28] Yan, W.; Wang, Q.; Lin, Q.; Li, M.; Petersen, J. L.; Shi, X. Chem.-Eur. J. 2011, 17, 5011.
[29] Zhang, Y.; Ye, X.; Petersen, J. L.; Li, M.; Shi, X. J. Org. Chem. 2015, 80, 3664.
[30] Wang, X.-J.; Zhang, L.; Lee, H.; Haddad, N.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2009, 11, 5026.
[31] Li, J.; Zhang, Y.; Wang, D.; Wang, W.; Gao, T.; Wang, L.; Li, J.; Huang, G.; Chen, B. Synlett 2010, 1617.
[32] Liu, X.; Li, J.; Chen, B. New J. Chem. 2013, 37, 965.
[33] Zhang, Y.; Li, X.; Li, J.; Chen, J.; Meng, X.; Zhao, M.; Chen, B. Org. Lett. 2012, 14, 26.
[34] Kamal, A.; Swapna, P. RSC Adv. 2013, 3, 7419.
[35] Singh, D. P.; Allam, B. K.; Singh, R.; Singh, K. N.; Singh, V. P. RSC Adv. 2016, 6, 15518.
[36] Ueda, S.; Su, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 8944.
[37] Ueda, S.; Ali, S.; Fors, B. P.; Buchwald, S. L. J. Org. Chem. 2012, 77, 2543.
[38] Lopes,A. B.; Wagner, P.; Souza, R. O. M. A.; Germain, N. L.; Uziel, J.; Bourguignon, J.-J.; Schmitt, M.; Miranda, L. S. M. J. Org. Chem. 2016, 81, 4540.
[39] Wen, J.; Zhu, L.-L.; Bi, Q.-W.; Shen, Z.-Q.; Li, X.-X.; Li, X.; Wang, Z.; Chen, Z. Chem.-Eur. J. 2014, 20, 974.
[40] Gu, C.-X.; Bi, Q.-W.; Gao, C.-K.; Wen, J.; Zhao, Z.-G.; Chen, Z. Org. Biomol. Chem. 2017, 15, 3396.
[41] Zhang, Y.-C.; Jin, R.; Li, L.-Y.; Chen, Z.; Fu, L.-M. Molecules 2017, 22, 1380.
[42] Guru, M. M.; Punniyamurthy, T. J. Org. Chem. 2012, 77, 5063.
[43] Stewart, S.; Harris, R.; Jamieson, C. Synlett 2014, 2480.
[44] Wu, L.; Guo, S.; Wang, X.; Guo, Z.; Yao, G.; Lin, Q.; Wu, M. Tetrahedron Lett. 2015, 56, 2145.
[45] Gavlik, K. D.; Lesogorova, S. G.; Sukhorukova, E. S.; Subbotina, J. O.; Slepukhin, P. A.; Benassi, E.; Belskaya, N. P. Eur. J. Org. Chem. 2016, 2700.
[46] Ai, W. M.S. Thesis, Dalian University of Technology, Dalian, 2008 (in Chinese). (艾文, 硕士论文, 大连理工大学, 大连, 2008.)
[47] Liu, G.-B.; Zhao, H.-Y.; Yang, H.-J.; Gao, X.; Li, M.-K.; Thiemannb, T. Adv. Synth. Catal. 2007, 349, 1637.
[48] Dong, J.; Jin, B.; Sun, P. Org. Lett. 2014, 16, 4540.
[49] Zhou, Z.; Liu, Q.-L.; Li, W.; Zhu, Y.-M. Heterocycles 2011, 83, 2057.
[50] Kale, R. R.; Prasad, V.; Hussain, H. A.; Tiwari, V. K. Tetrahedron Lett. 2010, 51, 5740.
[51] Shang, X.; Zhao, S.; Chen, W.; Chen, C.; Qiu, H. Chem.-Eur. J. 2014, 20, 1825.
[52] Liu, Q.-L.; Wen, D.-D.; Hang, C.-C.; Li, Q.-L.; Zhu, Y.-M. Helv. Chim. Acta 2010, 93, 1350.
[53] Zhou, J.; He, J.; Wang, B.; Yang, W.; Ren, H. J. Am. Chem. Soc. 2011, 133, 6868.
[54] Ryu, T.; Min, J.; Choi, W.; Jeon, W. H.; Lee, P. H. Org. Lett. 2014, 16, 2810.
[55] Khatun, N.; Modi, A.; Ali, W.; Patel, B. K. J. Org. Chem. 2015, 80, 9662.
[56] Li, J.; Zhou, H.; Zhang, J.; Yang, H.; Jiang, G. Chem. Commun. 2016, 52, 9589.

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