基于Huisgen内盐的环化反应研究进展
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
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).
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
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.
[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.
/
| 〈 |
|
〉 |