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2020 , Vol. 40 >Issue 8: 2338 - 2352

DOI: https://doi.org/10.6023/cjoc202002010

综述与进展

N-磺酰-1,2,3-三唑的合成方法及其在有机合成中的应用研究进展

  • 张文生 ,
  • 许文静 ,
  • 张斐 ,
  • 马春玉 ,
  • 马科友 ,
  • 李焱
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  • a 济源职业技术学院冶金化工系 河南济源 459000;
    b 焦作师范高等专科学校 合成技术研究所 河南焦作 454100;
    c 焦作职业技术学校 河南焦作 454100

收稿日期: 2020-02-10

  修回日期: 2020-04-16

  网络出版日期: 2020-05-11

基金资助

河南省教育厅自然科学重点研究计划（No.20B150014）和济源职业技术学院2020年重点科研课题（No.JZXY-2020-58）资助项目.

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Progress in Synthesis of N-Sulfonyl-1,2,3-triazole and Its Application in Organic Synthesis

  • Zhang Wensheng ,
  • Xu Wenjing ,
  • Zhang Fei ,
  • Ma Chunyu ,
  • Ma Keyou ,
  • Li Yan
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  • a Department of Metallurgy and Chemical Engineering, Jiyuan Vocational and Technical College, Jiyuan, Henan 459000;
    b Institute of Synthetic Technology, Jiaozuo Teachers College, Jiaozuo, Henan 454100;
    c Jiaozuo Vocational and Technological School, Jiaozuo, Henan 454100

Received date: 2020-02-10

  Revised date: 2020-04-16

  Online published: 2020-05-11

Supported by

Project supported by the Key Natural Science Research Program of Henan Education Department (No. 20B150014) and the Key Scientific Research Projects of Jiyuan Vocational and Technical College (No. JZXY-2020-58).

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摘要

N-磺酰-1，2，3-三唑是一类重要的五元含氮有机化合物，被广泛应用于合成各类含氮有机化合物，尤其是杂环或氨基取代芳环化合物.介绍了N-磺酰-1，2，3-三唑的主要合成方法，对其作为重氮亚胺和Rh-卡宾亚胺中间体的前体，通过开环构建各类有机化合物在2018~2019年期间的最新研究进展进行了综述.

关键词： N-磺酰-1,2,3-三唑; α-重氮亚胺; Rh-卡宾亚胺

本文引用格式

张文生 , 许文静 , 张斐 , 马春玉 , 马科友 , 李焱 . N-磺酰-1,2,3-三唑的合成方法及其在有机合成中的应用研究进展[J]. 有机化学, 2020 , 40(8) : 2338 -2352 . DOI: 10.6023/cjoc202002010

Abstract

N-Sulfonyl-1,2,3-triazole, an important class of five-membered nitrogen-containing organic compounds, has been found processing widespread application in the synthesis of various nitrogen-containing organic compounds, especially heterocyclic or amino-substituted aromatic rings. The synthetic methods of N-sulfonyl-1,2,3-triazole are introduced. Besides, the progress on constructions of various organic compounds via ring-opening reaction of N-sulfonyl-1,2,3-triazoles as precursor of α-diazoimine and Rh-carbene imine intermediates in the past two years is reviewed.

Key words： N-sulfonyl-1,2,3-triazole; α-diazoimine; Rh-carbene imine

参考文献

[1] (a) Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972.
(b) Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed. 2012, 51, 862.
(c) Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2013, 52, 1371.
(d) Davies, H. M. L.; Alford, J. S. Chem. Soc. Rev. 2014, 43, 5151.
(e) Wang, Y.; Lei, X.; Tang, Y. Synlett 2015, 26, 2051.
(f) Anbarasan, P.; Yadagiri, D.; Rajasekar, S. Synthesis 2014, 46, 3004.
(g) Hockey, S. C.; Henderson, L. C. Aust. J. Chem. 2015, 68, 1796.
(h) Jiang, Y.; Sun, R.; Tang, X.-Y.; Shi, M. Chem.-Eur. J. 2016, 22, 17910.
(i) Volkova, Y. A.; Gorbatov, S. A. Chem. Heterocycl. Compd. 2016, 52, 216.
(j) Li, Y.; Yang, H.-J.; Zhai, H.-B. Chem.-Eur. J. 2018, 24, 12757.
[2] (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
(b) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192.
[3] (a) Bae, I.; Han, H.; Chang, S. J. Am. Chem. Soc. 2005, 127, 2038.
(b) Zhang, W.-S.; Xu, W.-J.; Kuang, C.-X. Chin. J. Org. Chem. 2015, 35, 2059(in Chinese). (张文生, 许文静, 匡春香, 有机化学, 2015, 35, 2059.)
[4] Yoo, E. J.; Ahlquist, M.; Kim, S. H.; Bae, I.; Fokin, V. V.; Sharpless, K. B.; Chang, S. Angew. Chem., Int. Ed. 2007, 46, 1730.
[5] Wang, F.; Fu, H.; Jiang, Y.-Y.; Zhao, Y.-F. Adv. Synth. Catal. 2008, 350, 1830.
[6] Raushel, J.; Fokin, V. V. Org. Lett. 2010, 12, 4952.
[7] Liu, Y.-T.; Wang, X.-Y.; Xu, J.-M.; Zhang, Q.; Zhao, Y.; Hu, Y.-F. Tetrahedron 2011, 67, 6294.
[8] Zhang, W.-S.; Xu, W.-J. Chem. Heterocycl. Compd. 2016, 52, 192.
[9] Zhang, W.-S.; Xu, W.-J.; Zhang, F. Heterocycl. Commun. 2016, 22, 165.
[10] Rajasekar, S.; Anbarasan, P. Chem.-Asian J. 2019, 14, 4563.
[11] Garlets Z. J.; Davies, H. M. L. Org. Lett. 2018, 20, 2168.
[12] Kubiak, II, R. W.; Davies, H. M. L. Org. Lett. 2018, 20, 3771.
[13] Tian, M.-M.; Liu, B.-X.; Sun, J.-A.; Li, X.-W. Org. Lett. 2018, 20, 4946.
[14] Kahar, N. M.; Nabar, K. U.; Jadhav, P. P.; Dawande, S. G. Asian J. Org. Chem. 2019, 8, 79.
[15] (a) Rajasekar, S.; Anbarasan, P. Org. Lett. 2019, 21, 3067.
(b) Rajasekar, S.; Anbarasan, P. J. Org. Chem. 2019, 84, 7747.
[16] Mi, P.-B.; Wang, H.-N.; Zhao, R.; Song, J.-N. Eur. J. Org. Chem. 2018, 6, 759.
[17] Jia, R.-M.; Meng, J.; Leng, J.-Y.; Yu, X.-X.; Deng, W.-P. Chem.-Asian J. 2018, 13, 2360.
[18] Pal, K.; Hoque, A.; Volla, C. M. R. Chem.-Eur. J. 2018, 24, 2558
[19] Pal, K.; Sontakke, G. S.; Volla, C. M. R. Org. Lett. 2019, 21, 3716.
[20] Chen, Y.-H.; Dong, S.-X.; Xu, X.; Liu, X.-H.; Feng, X.-M. Angew. Chem., Int. Ed. 2018, 57, 16554.
[21] Alcaide, B.; Almendros, P.; Fernández, I.; Martínez del Campo, T.; Palop, G.; Toledano-Pinedo, M.; Delgado-Martίnez, P. Adv. Synth. Catal. 2019, 361, 1160.
[22] Kaladevi, S.; Kamalraj, M.; Altia, M.; Rajasekar, S.; Anbarasan, P. Chem. Commun. 2019, 55, 4507.
[23] Xing, S.-Y.; Xia, H.-Y.; Wang, X.; Wu, D.; Xu, X.-R.; Wang, Y.-R.; Su, K.; Zhu, B.-L.; Guo, J.-S. Org. Chem. Front. 2019, 6, 3121.
[24] Liu, Y.; Xie, P.; Li, J.-G.; Bai, W.-J.; Jiang, J. Org. Lett. 2019, 21, 4944.
[25] Liu, S.-Y.; Yao, W.-F.; Liu, Y.; Wei, Q.-H.; Chen, J.-H.; Wu, X.; Xia, F.; Hu, W.-H. Sci. Adv. 2017, 3, e1602467.
[26] Ma, X.-J.; Xie, X.-M.; Liu, L.; Xia, R.; Li, T.-Y.; Wang, H.-X. Chem. Commun. 2018, 54, 1595.
[27] Yu, S.-S.; An, Y.-H.; Wang, W.-L.; Xu, Z.-F.; Li, C.-Y. Adv. Synth. Catal. 2018, 360, 2125.
[28] Yadagiri, D.; Chaitanya, M.; Reddy, A. C. S.; Anbarasan, P. Org. Lett. 2018, 20, 3762.
[29] Liu, Z.; Du, Q.-C.; Zhai, H.-B.; Li, Y. Org. Lett. 2018, 20, 7514.
[30] Ma, X.-J.; Liu, L.; Wang, J.-Y.; Xi, X.-L.; Xie, X.-M.; Wang, H.-X. J. Org. Chem. 2018, 83, 14518.
[31] Xu, Z.-F.; Shan, L.-H.; Zhang, W.; Cen, M.-J.; Li, C.-Y. Org. Chem. Front. 2019, 6, 1391.
[32] Zhu, C.-Z.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2019, 361, 3430.
[33] Xu, Z.-F.; An, Y.-H.; Chen, Y.-D.; Duan, S.-G. Tetrahedron Lett. 2019, 60, 1849.
[34] Makarov, A. S.; Uchuskin, M. G.; Hashmi, A. S. K. Chem. Sci. 2019, 10, 8583.
[35] Bosmani, A.; Guarnieri-Ibáñez, A.; Goudedranche, S.; Besnard, C.; Lacour, J. Angew. Chem., Int. Ed. 2018, 57, 7151.
[36] Strelnikova, J. O.; Rostovskii, N. V.; Starova, G. L.; Khlebnikov, A. F.; Novikov, M. S. J. Org. Chem. 2018, 83, 11232.
[37] Khaidarov, A. R.; Rostovskii, N. V.; Zolotarev, A. A.; Khlebnikov, A. F.; Novikov, M. S. J. Org. Chem. 2019, 84, 3743.
[38] Khaidarov, A. R.; Rostovskii, N. V.; Starova1, G. L.; Khlebnikov, A. F.; Novikov, M. S. Chem. Heterocycl. Compd. 2018, 54, 946.
[39] Furukawa, A.; Hata, T.; Shigeta, M.; Urabe, H. Tetrahedron Lett. 2019, 60, 815.
[40] Ge, J.-M.; Wu, X.-L.; Bao, X.-G. Chem. Commun. 2019, 55, 6090.
[41] (a) Zhao, Q.; Miura, T.; Murakami, M. Chem. Lett. 2019, 48, 510.
(b) Miura, T.; Zhao, Q.; Murakami, M. Angew. Chem., Int. Ed. 2017, 56, 16645.
[42] Zhu, C.-Z.; Wei, Y.; Shi, M. Org. Chem. Front. 2019, 6, 2884.
[43] Sontakke, G. S.; Pal, K.; Volla, C. M. R. J. Org. Chem. 2019, 84, 12198.
[44] Li, Z.; Wei, Q.-H.; Song, L.-L.; Han, W. Y. J.; Wu, X.; Zhao, Y.; Xia, F.; Liu, S. Y. Org. Lett. 2019, 21, 6413.
[45] Jiang, Y.; Wang, Q.; Sun, R.; Tang, X.-Y.; Shi, M. Org. Chem. Front. 2016, 3, 744.
[46] Li, L.-H.; Jiang, Y.; Hao, J.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2017, 359, 3304.
[47] Xu, Z.-F.; Dai, H.-C.; Shan, L.-H.; Li, C.-Y. Org. Lett. 2018, 20, 1054.
[48] Yang, D.-D.; Shan, L.-H.; Xu, Z.-F.; Li, C.-Y. Org. Biomol. Chem. 2018, 16, 1461.
[49] Wilkerson-Hill, S. M.; Haines, B. E.; Musaev, D. G.; Davies, H. M. L. J. Org. Chem. 2018, 83, 7939.
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