综述与进展

基于Huisgen内盐的环化反应研究进展

  • 刘奕奕 ,
  • 周荣
展开
  • a 国网湖南省电力有限公司电力科学研究院 长沙 410007;
    b 太原理工大学化学化工学院 太原 030024

收稿日期: 2019-03-21

  修回日期: 2019-04-20

  网络出版日期: 2019-05-06

基金资助

国家自然科学基金(No.21502135)、山西省高校科技创新(No.201802024)资助项目.

Progress in Annulation Reactions Based on Huisgen Zwitterion

  • Liu Yiyi ,
  • Zhou Rong
Expand
  • a State Grid Hunan Electric Power Corporation Limited Research Institute, Changsha 410007;
    b College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024

Received date: 2019-03-21

  Revised date: 2019-04-20

  Online published: 2019-05-06

Supported by

Project supported by the National Natural Science Foundation of China (No. 21502135), the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi Province (No. 201802024).

摘要

发展高效、高选择性的有机合成方法是有机化学的一项重要研究内容.近年来,叔膦与偶氮二甲酸酯加成形成的Huisgen内盐在氮杂环化合物的合成上显示出独特的优越性和高效性,吸引了众多有机化学家的研究兴趣,基于Huisgen内盐的环化反应得以大量报道.根据亲电试剂的种类不同,综述了Husigen内盐与羰基化合物、缺电子烯烃、亚胺以及其他亲电试剂的环化反应.

本文引用格式

刘奕奕 , 周荣 . 基于Huisgen内盐的环化反应研究进展[J]. 有机化学, 2019 , 39(9) : 2365 -2378 . DOI: 10.6023/cjoc201903041

Abstract

The development of highly efficient and selective synthetic methodologies is an important research task in organic chemistry. In recent years, the Huisgen zwitterions, a type of intermediates derived from nucleophilic addition of tertiary phosphine to azodicarboxylates, have shown unique superiority and efficiency in synthesis of azacyclic compounds, and therefore have attracted broad interest from organic chemists. A large number of annulation reactions based on Huisgen zwitterions have been reported. According to the types of electrophiles, the annulation reactions of Husigen zwitterions with carbonyl compounds, electron-deficient alkenes, imines, and other electrophiles are summarized, respectively.

参考文献

[1] Cadogan, J. I. G. Organophosphorus Reagents in Organic Synthesis, Academic Press, London, 1979.
[2] (a) Ye, L. -W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140.
(b) Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102.
(c) Marinetti, A.; Voituriez, A. Synlett 2010, 174.
(d) Wang, S.; Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Synlett 2011, 2766.
(e) Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724.
(f) Fan, Y.-C.; Kwon, O. Chem. Commun. 2013, 49, 11588.
(g) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927.
(h) Xiao, Y.; Sun, Z.; Guo, H.; Kwon, O. Beilstein J. Org. Chem. 2014, 10, 2089.
(i) Xie, P.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578.
(j) Xiao, Y.; Guo, H.; Kwon, O. Aldrichim. Acta 2016, 49, 3.
(k) Wang, T.; Han, X.; Zhong, F.; Yao, W.; Lu, Y. Acc. Chem. Res. 2016, 49, 1369.
(l) Zhou, R.; He, Z. Eur. J. Org. Chem. 2016, 1937.
[3] (a) Xu, S.; He, Z. RSC Adv. 2013, 3, 16885.
(b) Xu, S. L.; He, Z. J. Chin. J. Org. Chem. 2014, 34, 2438(in Chinese). (徐四龙, 贺峥杰, 有机化学, 2014, 34, 2438.)
(c) Karanam, P.; Reddy, G. M.; Koppolu, S. R.; Lin, W. Tetrahedron Lett. 2018, 59, 59.
(d) Liu, Y.; Sun, F.; He, Z. Tetrahedron Lett. 2018, 59, 4136.
[4] Quin, L. D. A Guide to Organophosphorus Chemistry, Wiley, New York, 2000, p. 379.
[5] Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
[6] Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. Chem. Rev. 2009, 109, 2551.
[7] Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
[8] Appel, R. Angew. Chem., Int. Ed. 1975, 14, 801.
[9] (a) Huisgen, R.; Blaschke, H.; Brunn, E. Tetrahedron Lett. 1966, 7, 405.
(b) Brunn, E.; Huisgen, R. Angew. Chem., Int. Ed. 1969, 8, 513.
(c) Itzstein, M. v.; Jenkins, I. D. Aust. J. Chem. 1983, 36, 557.
(d) Monge, D.; Jensen, K. L.; Marín, I.; Jørgensen, K. A. Org. Lett. 2011, 13, 328.
[10] Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520.
[11] Nair, V.; Biju, A. T.; Mathew, S. C.; Babu, B. P. Chem. Asian J. 2008, 3, 810.
[12] Košmrlj, J.; Ko?evar, M.; Polanc, S. Synlett 2009, 2217.
[13] Cookson, R. C.; Locke, J. M. J. Chem. Soc. 1963, 6062.
[14] Kolasa, T.; Miller, M. J. J. Org. Chem.1987, 52, 4978.
[15] Otte, R. D.; Sakata, T.; Guzei, I. A.; Lee, D. Org. Lett. 2005, 7, 495.
[16] (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
(b) Wei, Y.; Shi, M. Acc. Chem. Res. 2010, 43, 1005.
(c) Huang, Y.; Xie, P. Eur. J. Org. Chem. 2013, 6213.
(d) Wei, Y.; Shi, M. Chem. Rev. 2013, 113, 6659.
(e) Li, W.; Zhang, J. Chem. Soc. Rev. 2016, 45, 1657.
[17] Nair, V.; Biju, A. T.; Vinod, A. U.; Suresh, E. Org. Lett. 2005, 7, 5139.
[18] Dogan, H. N.; Duran, A.; Rollas, S.; Sener, G.; Armutak, Y.; Keyer Uysal, M. Med. Sci. Res. 1998, 26, 755.
[19] Wang, Z.-D.; Dong, N.; Wang, F.; Li, X.; Cheng, J.-P. Tetrahedron Lett. 2013, 54, 5473.
[20] Nair, V.; Mathew, S. C.; Biju, A. T.; Suresh, E. Angew. Chem., Int. Ed. 2007, 46, 2070.
[21] (a) Elguero, J. In Comprehensive Heterocyclic Chemistry, Vol. 5, Eds.:Katritzky, A. R.; Rees, C. W.; Potts, K. T., Pergamon, Ox-ford, 1984, p. 167.
(b) Elguero, J. In Comprehensive Heterocyclic Chemistry Ⅱ, Vol. 3, Eds.:Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Pergamon, Oxford, 1996, p. 1.
[22] (a) BraLa, M. F.; Cacho, M.; GarcMa, M. L.; Mayoral, E. P.; LNpez, B.; Pascual-Teresa, B.; Ramos, A.; Acero, N.; Llinares, F.; MuLozMingarro, D.; Lozach, O.; Meijer, L. J. Med. Chem. 2005, 48, 6843.
(b) Witherington, J.; Bordas, V.; Haigh, D.; Hickey, D. M. B.; Ife, R. J.; Rawlings, A. D.; Slingsby, B. P.; Smith, D. G.; Ward, R. W. Bioorg. Med. Chem. Lett. 2003, 13, 1581.
(c) Tewari, A. K.; Mishra, A. Bioorg. Med. Chem. 2001, 9, 715.
[23] Liu, W.; Khedkar, V.; Baskar, B.; Schürmann, M.; Kumar, K. Angew. Chem., Int. Ed. 2011, 50, 6900.
[24] Baskar, B.; Wittstein, K.; Sankar, M. G.; Khedkar, V.; Schürmann, M.; Kumar, K. Org. Lett. 2012, 14, 5924.
[25] Papafilippou, A.; Terzidis, M. A.; S.-S.Julia.; Tsoleridis, C. A. Tetrahedron Lett. 2011, 52, 1306.
[26] (a) McCleverty, J. A.; Meyer, T. J. Comprehensive Coordination Chemistry Ⅱ, Elsevier Ltd, Boston, 2003.
(b) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
(c) Börner, A. Phosphorus Ligands in Asymmetric Catalysis, Wiley-VCH, Weinheim, Germany, 2008.
(d) Zhou, Q.-L. Privileged Chiral Ligands and Catalysts, Wiley-VCH, Weinheim, Germany, 2011.
(e) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
[27] Nair, V.; Biju, A. T.; Mohanan, K.; Suresh, E. Org. Lett. 2006, 8, 2213.
[28] Chakravarty, M.; Kumar, N. N. B; Sajna, K. V.; Swamy, K. C. K. Eur. J. Org. Chem. 2008, 4500.
[29] Lü, R.; Cheng, X.; Zheng, X.; Ma, S. Chem. Commun. 2014, 50, 1537.
[30] (a) Kazmo, Y.; Akira, M.; Norihiko, M.; Toshiio, M.; Kazutaka, A. Shigera, I. Pestic. Sci. 1999, 55, 161.
(b) Gursoy, A.; Demirayak, M. S.; Çapan, G.; Erol, K.; Vural, K. Eur. J. Med. Chem. 2000, 35, 359.
(c) Badawey, E. A. M.; El-Ashmawey, I. M. Eur. J. Med. Chem. 1998, 33, 349.
[31] Yamazaki, S.; Maenaka, Y.; Fujinami, K.; Mikata, Y. RSC Adv. 2012, 2, 8095.
[32] Yang, C.; Li J.; Zhou, R.; Chen, X.; Gao, Y.; He, Z. Org. Biomol. Chem. 2015, 13, 4869.
[33] Yang, C.; Chen, X.; Tang, T.; He, Z. Org. Lett. 2016, 18, 1486.
[34] Li, Y.; Zhang, H.; Wei, R.; Miao, Z. Adv. Synth. Catal. 2017, 359, 4158.
[35] Lian, Z.; Guan, X.-Y.; Shi, M. Tetrahedron 2011, 67, 2018.
[36] Sankar, M. G.; Garcia-Castro, M.; Wang, Y.; Kumar, K. Asian J. Org. Chem. 2013, 2, 646.
[37] Alizadeh, A. Helv. Chim. Acta 2005, 88, 2777.
[38] Cui, S.-L.; Wang, J.; Wang, Y.-G. Org. Lett. 2008, 10, 13.
[39] Sun, Y.; Jiang, Z.; Hong, D.; Lu, P.; Wang, Y.; Lin, X. Tetrahedron 2010, 66, 2427.
[40] Zhang, W.; Zhu, Y.; Wei, D.; Tang, M. J. Comput. Chem. 2012, 33, 715.
[41] Saha, J.; Lorenc, C.; Surana, B.; Peczuh, M. W. J. Org. Chem. 2012, 77, 3846.
[42] Yang, C.; Liu, W.; He, Z.; He, Z. Org. Lett. 2016, 18, 4936.

文章导航

/