基于烯基叠氮合成含氮杂环化合物的研究进展

doi:10.6023/cjoc201711043

摘要/Abstract

自1910年首次被报道以来，烯基叠氮类化合物受到了化学工作者们广泛的关注.作为一类重要的有机合成中间体，尤其是在过渡金属催化下合成氮杂环类化合物方面，烯基叠氮类化合物有着广泛的应用.主要综述了烯基叠氮类化合物在构建含氮杂环化合物领域的研究进展.

关键词: 烯基叠氮, 合成, 含氮杂环

Vinyl azides have been extensively studied in organic synthesis since 1910. As a series of important intermediates, vinyl azides have a wide range of applications in recent years, especially in the synthesis of heterocyclic compounds catalyzed by transition-metals. The progress of the construction of aza-heterocyclic compounds in the field of organic synthesis is reviewed.

Key words: vinyl azide, synthesis, aza-heterocycle

引用此文

王钰莹, 刘莉, 王也铭. 基于烯基叠氮合成含氮杂环化合物的研究进展[J]. 有机化学, 2018, 38(5): 1009-1028.

Wang Yuying, Liu Li, Wang Yeming. Advances Research in Synthesis of Aza-heterocyclic Compounds Involving Vinyl Azides[J]. Chin. J. Org. Chem., 2018, 38(5): 1009-1028.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Forster, M. O.; Newman, S. H. J. Chem. Soc. 1910, 97, 2570.
[2] Hemetsberger, H.; Knittel, D.; Weidmann, H. Monatsh. Chem. 1969, 100, 1599.
[3] Zhu, W.; Ma, D.-W. Chem. Commun. 2004, 888.
[4] Hassner, A.; Levy, L. A. J. Am. Chem. Soc. 1965, 87, 4203.
[5] Harvey, G. R.; Ratts, K. W. J. Org. Chem. 1966, 31, 3907.
[6] Priebe, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 736.
[7] Chou, T. S.; Lee, S. J.; Peng, M. L.; Sun D. J.; Chou, S. S. P. J. Org. Chem. 1988, 53, 3027.
[8] Fu, J.-K.; Giuseppe, Z.; Edward, A. A.; Bi, X.-H. Chem. Soc. Rev. 2017, 46, 7208.
[9] Zhang, L.; Sun, G.; Bi, X.-H. Chem.-Asian J. 2016, 11, 3018.
[10] Yan, J.; Ji, X.-Y.; Hua, S.-G.; Wang, J. Chin. J. Org. Chem. 2018, 38, 791(in Chinese). (严珺, 姬晓悦, 花书贵, 王静, 有机化学, 2018, 38, 791.)
[11] (a) Neber, P. W.; Burgard, A. Justus Liebigs Ann. Chem. 1932, 493, 281.
(b) Neber, P. W.; Huh, G. Justus Liebigs Ann. Chem. 1935, 515, 283.
[12] (a) Würthwein, T.; Hergenröther, T.; Quast, H. Eur. J. Org. Chem. 2002, 1750.
(b) Banert, K.; Meier, B. Angew. Chem., Int. Ed. 2006, 45, 4015.
[13] (a) Smolinsky, G. J. Am. Chem. Soc. 1961, 83, 4483.
(b) Smolinsky, G. J. Org. Chem. 1962, 27, 3557.
[14] Alves, M. J.; Bickley, J. F.; Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1999, 1399.
[15] Patonay, T.; Jeko, J.; Juhasz-Toth, E. Eur. J. Org. Chem. 2008, 1441.
[16] Kumar, R.; Nath, M.; Tyrrell, D. L. J. J. Med. Chem. 2002, 45, 2032.
[17] Pinhoe Melo, T. M. V. D.; Lopes, C. S. J.; Cardoso, A. L.; Rocha Gonsalves, A. M. d'A. Tetrahedron 2001, 57, 6203.
[18] Alonso-Cruz, C. R.; Kennedy, A. R.; Rodríguez, M. S.; Suárez, E. Tetrahedron Lett. 2007, 48, 7207.
[19] Alonso-Cruz, C. R.; Kennedy, A. R.; Rodríguez, M. S.; Suárez, E. J. Org. Chem. 2008, 73, 4116.
[20] Timen, A. S.; Risberg, E.; Somfai, P. Tetrahedron Lett. 2003, 44, 5339.
[21] Alajarín, M.; Orenes, R.; Vidal, Á.; Pastor, A. Synthesis 2003, 49.
[22] Singh, P. N. D.; Carter, C. L.; Gudmundsdóttir, A. D. Tetrahedron Lett. 2003, 44, 6763.
[23] Furin, G. G.; Gatilov, Y. V.; Bagrynskay, I. Y.; Zhuzhgov, E. L. J. Fluorine Chem. 2001, 110, 21.
[24] Banert, K.; Kohler, F.; Kowski, K.; Meier, B.; Muller, B.; Rademacher, P. Chem.-Eur. J. 2002, 8, 5089.
[25] Banert, K.; Fotsing, J. R.; Hagedorn, M.; Reisenauer, H. P.; Maier, G. Tetrahedron 2008, 64, 5645.
[26] Banert, K.; Hagedorn, M.; Wutke, J.; Ecorchard, P.; Schaarschmidt, D.; Lang, H. Chem. Commun. 2010, 46, 4058.
[27] Banert, K.; Kçhler, F.; Melzer, A.; Scharf, I.; Rheinwald, G.; Ruffer, T.; Lang, H.; Herges, R.; Heß, K.; Ghavtadze, N.; Wurthwein, E.-U. Chem.-Eur. J. 2011, 17, 10071.
[28] Banert, K.; Meier, B.; Penk, E.; Saha, B.; Wurthwein, E.-U.; Grimme, S.; Ruffer, T.; Schaarschmidt, D.; Lang, H. Chem.-Eur. J. 2011, 17, 1128.
[29] Banert, K.; Ihle, A.; Kuhtz, A.; Penk, E.; Saha, B.; Würthwein, E.-U. Tetrahedron 2013, 69, 2501.
[30] Chen, F.; Shen, T.; Cui, Y.-X.; Jiao, N. Org. Lett. 2012, 14, 4926.
[31] Donthiri, R. R.; Samanta, S.; Adimurthy, S. Org. Biomol. Chem. 2015, 13, 10113.
[32] Chiba, S.; Wang, Y.-F.; Lapointe, G.; Narasaka, K. Org. Lett. 2008, 10, 313.
[33] Ng, E. P. J.; Wang, Y.-F.; Hui, B. W.-Q.; Lapointe, G.; Chiba, S. Tetrahedron 2011, 67, 7728.
[34] Wang, Y.-F.; Toh, K. K.; Chiba, S.; Narasaka, K. Org. Lett. 2008, 10, 5019.
[35] Ng, E. P. J.; Wang, Y.-F.; Chiba, S. Synlett 2011, 783.
[36] Yu, W.-W.; Chen, W.-T.; Liu, S.; Shao, J.-A.; Shao, Z.-Y.; Lin, H.-L.; Yu, Y.-P. Tetrahedron 2013, 69, 1953.
[37] Chen, W.-T.; Shao, J.-A.; Li, Z.; Giulianotti, M. A.; Yu, Y.-P. Can. J. Chem. 2012, 90, 214.
[38] Wu, Y.-F.; Zhu, L.; Yu, Y.-H.; Luo, X.-S.; Huang, X.-L. J. Org. Chem. 2015, 80, 11407.
[39] Pawar, S. K.; Sahani, R. L.; Liu, R.-S. Chem.-Eur. J. 2015, 21, 10843.
[40] Zhu, L.; Yu, Y.-H.; Mao, Z.-F.; Huang, X.-L. Org. Lett. 2015, 17, 30.
[41] Cludius-Brandt, S.; Kupracz, L.; Kirschning, A. Beilstein J. Org. Chem. 2013, 9, 1745.
[42] Dong, H.-J.; Shen, M.-H.; Redford, J. E.; Stokes, B. J.; Pumphrey, A. L.; Driver, T. G. Org. Lett. 2007, 9, 5191.
[43] Farney, E. P.; Yoon, T. P. Angew. Chem., Int. Ed. 2014, 53, 793.
[44] Zhang, L.; Sun, G.; Bi, X.-H. Chem.-Asian J. 2016, 11, 3018.
[45] Nie, Y.-B.; Wang, L.; Ding, M.-W. J. Org. Chem. 2012, 77, 696.
[46] Wang, Y.; Xie, H.; Pan, Y.-R.; Ding, M. W. Synthesis 2014, 336.
[47] Liu, S.; Shao, J.-A.; Guo, X.; Luo, J.; Zhao, M.-H.; Zhang, G.-L.; Yu, Y.-P. Tetrahedron 2014, 70, 1418.
[48] Luo, J.; Chen, W.-T.; Shao, J.-A.; Liu, X.-Y.; Shu, K.; Tang, P.; Yu, Y.-P. RSC Adv. 2015, 5, 55808.
[49] Xiang, L.-K.; Niu, Y.-N.; Pang, X.-B.; Yang, X.-D.; Yan, R.-L. Chem. Commun. 2015, 51, 6598.
[50] Tiwari, D. K.; Maurya, R. A.; Nanubolu, J. B. Chem.-Eur. J. 2016, 22, 526.
[51] Adiyala, P. R.; Borra, S.; Kamal, A.; Maurya, R. A. Eur. J. Org. Chem. 2016, 1269.
[52] Zhu, Z.-Z.; Tang, X.-D.; Li, J.-X.; Li, X.-W.; Wu, W.-Q.; Deng, G.-H.; Jiang, H.-F. Org. Lett. 2017, 19, 1370.
[53] Hu, J.-T.; Cheng, Y.-F.; Yang, Y.-Q.; Rao, Y. Chem. Commun. 2011, 47, 10133.
[54] (a) Zou, H.-B.; Zhu, H.-J.; Shao, J.-A.; Wu, J.-W.; Chen, W.-T.; Giulianotti, M. A.; Yu, Y.-P. Tetrahedron 2011, 67, 4887.
(b) Li, Y.; Hong, D.; Lu, P.; Wang, Y. G. Tetrahedron Lett. 2011, 52, 4161.
[55] Zhang, G.-L.; Ni, H.-C.; Chen, W.-T.; Shao, J.-A.; Liu, H.; Chen, B.-H.; Yu, Y.-P. Org. Lett. 2013, 15, 5967.
[56] Huang, W.; Liu, S.; Chen, B.-H.; Guo, X.; Yu, Y.-P. RSC Adv. 2015, 5, 32740.
[57] (a) Wang Y.-F.; Chiba, S. J. Am. Chem. Soc. 2009, 131, 12570.
(b) Wang, Y. F.; Toh, K. K.; Ng, E. P. J.; Chiba, S. J. Am. Chem. Soc. 2011, 133, 6411.
[58] Sajna, K. V.; Kumara Swamy, K. C. J. Org. Chem. 2012, 77, 8712.
[59] Shao, Z.-Y.; Pan, Q.-H.; Chen, J.; Yu, Y.-P.; Zhang, G.-L. Tetrahedron 2012, 68, 6565.
[60] Nishimura, Y.; Hidetsura, C. H. Synlett 2015, 233.
[61] Shao, J.-A.; Liu, X.-Y.; Shu, K.; Tang, P.; Luo, J.; Chen, W.-T.; Yu, Y.-P. Org. Lett. 2015, 17, 4502.
[62] Knittel, D. Synthesis 1985, 186.
[63] Stokes, B. J.; Dong, H.; Leslie, B. E.; Pum-phrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500.
[64] Hong, D.; Chen, Z.-B.; Lin, X.-F.; Wang, Y.-G. Org. Lett. 2010, 12, 4608.
[65] Zhu, X.; Wang, Y.-F.; Zhang, F.-L.; Chiba, S. Chem.-Asian J. 2014, 9, 2458.
[66] Wang, Q.-L.; Huang, J.; Zhou, L. Adv. Synth. Catal. 2015, 357, 2479.
[67] (a) Yang, Y. Y.; Shou, W. G.; Chen, Z. B.; Hong, D. J. Org. Chem. 2008, 73, 3928.
(b) Chen, Z. B.; Hong, D.; Wang, Y.-G. J. Org. Chem. 2009, 74, 903.
[68] Wang, Y.-F.; Toh, K.-K.; Lee, J.-Y.; Chiba, S. Angew. Chem., Int. Ed. 2011, 50, 5927.
[69] Wang, Y.-F.; Lonca, G. H.; Chiba, S. Angew. Chem., Int. Ed. 2014, 53, 1067.
[70] Liu, K.; Chen, S.; Li, X.-G.; Liu, P.-N. J. Org. Chem. 2016, 81, 265.
[71] Zhu, Z.-Z.; Tang, X.-D.; Li, X.-W.; Wu, W.-Q.; Deng, G.-H.; Jiang, H.-F. J. Org. Chem. 2016, 81, 1401.
[72] Wang, Y. F.; Lonca, G. H.; Runigo, M. L.; Chiba, S. Org. Lett. 2014, 16, 4272.
[73] Mackay, E. G.; Studer, A. Chem.-Eur. J. 2016, 22, 13455.
[74] Sun, X.-Y.; Yu, S.-Y. Chem. Commun. 2016, 52, 10898.
[75] Chen, W.-T.; Hu, M.; Wu, J.-W.; Zou, H.-B.; Yu, Y.-P. Org. Lett. 2010, 12, 3863.
[76] Donthiri, R. R.; Pappula, V.; Reddy, N. N. K.; Bairagi, D.; Adimurthy, S. J. Org. Chem. 2014, 79, 11277.
[77] Adiyala, P. R.; Mani, G. S.; Nanubolu, J. B.; Shekar, K. C.; Maurya, R. A. Org. Lett. 2015, 17, 4308.
[78] Dinda, B. K.; Jana, A. K.; Mal, D. Chem. Commun. 2012, 48, 3999.
[79] Guo, S.-S.; Chen, B.-H.; Guo, X.; Zhang, G.-L.; Yu, Y.-P. Tetrahedron 2015, 71, 9371.
[80] Guo, S.-S.; Chen, B.-H.; Zhao, D.-H.; Chen, W.-T.; Zhang, G.-L. Adv. Synth. Catal. 2016, 358, 3010.
[81] Xu, H.-D.; Zhou, H.; Pan, Y.-P.; Ren, X.-T.; Wu, H.; Han, M.; Han, R.-Z.; Shen, M.-H. Angew. Chem., Int. Ed. 2016, 55, 2540.