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

doi:10.6023/cjoc201710018

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1052-1064.DOI: 10.6023/cjoc201710018 Previous Articles Next Articles

Reviews

N²-取代1,2,3-三唑的合成研究进展

朱莉莉^a, 张辉^a, 王春杰^a, 陈自立^b

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 发布日期:2018-01-10
通讯作者: 朱莉莉,E-mail:lily77cq@163.com;陈自立,E-mail:zilichen@ruc.edu.cn E-mail:lily77cq@163.com;zilichen@ruc.edu.cn
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.

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

Zhu Lili^a, Zhang Hui^a, Wang Chunjie^a, Chen Zili^b

a School of Chemistry and Chemical Engneering, Zhoukou Normal University, Zhoukou 466001;
b Department of Chemistry, Renmin University of China, Beijing 100872

Received:2017-12-16 Revised:2017-12-20 Published:2018-01-10
Contact: 10.6023/cjoc201710018 E-mail:lily77cq@163.com;zilichen@ruc.edu.cn
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).

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

Cite this article

Zhu Lili, Zhang Hui, Wang Chunjie, Chen Zili. Recent Progress in the Synthesis of N²-Substituted 1, 2, 3-Triazoles[J]. Chin. J. Org. Chem., 2018, 38(5): 1052-1064.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

N²-取代1,2,3-三唑的合成研究进展

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

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.
[2]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[3]	Boyu Yan, Jieliang Wu, Jinfei Deng, Dan Chen, Xiushen Ye, Qiuli Yao. Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3055-3066.
[4]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[5]	Xiao Song, Jing Qing, Jun Li, Xuelei Jia, Fusong Wu, Junrong Huang, Jian Jin, Hengzhi You. Copper-Catalyzed Asymmetric Allyl Alkylation Using Grignard Reagents under Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3174-3179.
[6]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
[7]	Yuzhuo Chen, Hongmei Sun, Liang Wang, Fangzhi Hu, Shuaishuai Li. Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2323-2337.
[8]	Fen Huang, Weiwei Luo, Jun Zhou. Research Progress of Polychloroalkylation Based on C—H Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2368-2390.
[9]	Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.
[10]	Zhijun Ren, Weiwei Luo, Jun Zhou. Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2026-2039.
[11]	Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225.
[12]	Jun Lu, Qichuang Li, Renxiao Liang, Yixia Jia. Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1875-1882.
[13]	Li Sun, Guoxin Song, Jiale Han, Jiyu Li, Yue Zhao, Luhua Yang, Feng Zhang, Kun Zhao, Biming Mao. Electrochemical Allylic Alkylation of Morita-Baylis-Hillman Adducts and N-Hydroxyphthalimide Esters towards C(sp³)—C(sp³) Bond Formation [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1574-1583.
[14]	Jingpeng Li, Shuntao Huang, Qi Yang, Weiqiang Li, Teng Liu, Chao Huang. A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1550-1558.
[15]	Nan Jiang, Guanjie Huang, Yan Hu, Bo Wang. Ruthenium-Catalyzed C—H [4＋2] Annulation of Quinazolinones with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1537-1549.

N2-取代1,2,3-三唑的合成研究进展