Recent Advances on Multicomponent Reactions Based on the Transamination Process of Electron Deficient Enamines

doi:10.6023/cjoc201312016

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 876-885.DOI: 10.6023/cjoc201312016 Previous Articles Next Articles

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基于缺电子烯胺交叉氨化过程的多组分反应研究进展

曹硕^a, 景艳锋^a, 刘云云^a,b, 万结平^a,b

a 江西师范大学化学化工学院南昌 330022;
b 教育部功能有机小分子重点实验室江西师范大学南昌 330022

收稿日期:2013-12-15 修回日期:2014-01-05 发布日期:2014-01-10
通讯作者: 万结平 E-mail:wanjieping@jxnu.edu.cn
基金资助:
国家自然科学基金（No. 21102059）、江西省教育厅基金（No. GJJ13245）和江西师范大学青年英才计划资助项目.

Recent Advances on Multicomponent Reactions Based on the Transamination Process of Electron Deficient Enamines

Cao Shuo^a, Jing Yanfeng^a, Liu Yunyun^a,b, Wan Jieping^a,b

a College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022;
b Key Laboratory of Functional Small Organic Molecules, Ministry of Education, Jiangxi Normal University, Nanchang 330022

Received:2013-12-15 Revised:2014-01-05 Published:2014-01-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21102059), the Project from the Department of Education of Jiangxi Province (No. GJJ13245) and the Sponsored Program for Cultivating Youths of Outstanding Ability in Jiangxi Normal University.

Electron deficient enamines bear several different nucleophilic and eletrophilic sites in their structures, they can also serve as donors of C=C bonds in organic reactions. Therefore, electron deficient enamines have been broadly employed in organic synthesis via various nucleophilic, electrophilic transformation and cycloaddition. Based on the research interest and works of our group in the chemistry of electron deficient enamines, the research advances on multicomponent reactions (MCRs) are reviewed based on the transamination of electron deficient enamines with ammomium, amines, enamines, ureas and thioureas as key transformation.

Key words: electron deficient enamine, transamination, multicomponent reactions, heterocycle

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Cao Shuo, Jing Yanfeng, Liu Yunyun, Wan Jieping. Recent Advances on Multicomponent Reactions Based on the Transamination Process of Electron Deficient Enamines[J]. Chin. J. Org. Chem., 2014, 34(5): 876-885.

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References

[1] Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471.

[2] Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 3, 167.

[3] Kuehne, M. E. J. Am. Chem. Soc. 1959, 81, 5400.

[4] Malhotra, S. K.; Hostynek, J. J.; Lundin, A. F. J. Am. Chem. Soc. 1968, 90, 6565.

[5] Hayakawa, Y.; Yokoyama, K.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1799.

[6] Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem. Eur. J. 2003, 9, 2797.

[7] Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.

[8] Enders, D.; Huttl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861.

[9] List, B. Acc. Chem. Res. 2004, 37, 548.

[10] Han, J.; Paton, R. S.; Xu, B.; Hammond, G. B. Synthesis 2013, 463.

[11] Xu, D.-Q.; Xia, H.-B.; Luo, S.-P.; Tang, J.; Zhang, S.; Jiang, J.-R.; Xu, Z.-Y. Angew. Chem., Int. Ed. 2009, 48, 3821.

[12] Sulzer-Mossé, S.; Alexakis, A. Chem. Commun. 2007, 3123.

[13] Han, Y.; Sun, J.; Sun, Y.; Gao, H.; Yan, C. G. Chin. J. Org. Chem. 2012, 32, 1557 (in Chinese).

(韩莹, 孙晶, 孙岩, 高红, 颜朝国, 有机化学, 2012, 32, 1557.)

[14] Li, M.; Guo, W. S.; Wen, L. R.; Yang, H. Z. Chin. J. Org. Chem. 2006, 26, 1192 (in Chinese).

(李明, 郭维斯, 文丽荣, 杨华铮, 有机化学, 2006, 26, 1192.)

[15] Wang, Y.-F.; Izawa, T.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1982, 104, 6465.

[16] Neumann, J. J.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 7790.

[17] Refvik, M. D.; Schwan, A. L. J. Org. Chem. 1996, 61, 4232.

[18] Yang, Q.-Z.; Siri, O.; Braunstein, P. Chem. Commun. 2005, 2660.

[19] Lorber, C.; Vendier, L. Dalton Trans. 2013, 42, 12203.

[20] Gupta, S.; Agarwal, P. K.; Kundu, B. Tetrahedron Lett. 2010, 51, 1887.

[21] Liu, Y. Y.; Zhou, R. H.; Wan, J.-P. Synth. Commun. 2013, 43, 2475.

[22] Al-Saleh, El-Apasery, M. A.; Abdel-Aziz, R. S.; Elnagdi, M. H. J. Heterocycl. Chem. 2005, 42, 563.

[23] Zhou, Z.-Z.; Liu, F.-S.; Shen, D.-S.; Tan, C.; Luo, L.-Y. Inorg. Chem. Commun. 2011, 14, 659.

[24] Al-Saleh, B.; Abdelkhalik, M. M.; Eltoukhy, A. M.; Elnagdi, H. J. Heterocycl. Chem. 2002, 39, 1035.

[25] Reddy, G. J.; Latha, D.; Thirupathaiah, C.; Rao, K. S. Tetrahedron Lett. 2005, 46, 301.

[26] Kantevari, S.; Chary, M. V.; Vuppalapati, S. V. N. Tetrahedron 2007, 63, 13024.

[27] Kantevary, S.; Chary, M. V.; Vuppalapati, S. V. N.; Lingaiah, N. J. Heterocycl. Chem. 2008, 45, 1099.

[28] Kantevary, S.; Patpi, S. R.; Addla, D.; Putapatri, S. R.; Sridhar, B.; Yogeeswari, P.; Sriram, D. ACS Comb. Sci. 2011, 13, 427.

[29] Kantevary, S.; Addla, D.; Sridhar, B. Synthesis 2010, 3745.

[30] Kantevary, S.; Putapatri, S. R. Synlett 2010, 2251.

[31] Siddiqui, Z. N.; Ahmed, N.; Farooq, F.; Khan, K. Tetrahedron Lett. 2013, 54, 3599.

[32] Wan, J.-P.; Gan, S.-F.; Sun, G.-L.; Pan, Y.-J. J. Org. Chem. 2009, 74, 2862.

[33] Wan, J.-P.; Wang, C. P.; Pan, Y. J. Tetrahedron 2011, 67, 922.

[34] Muthusaravanan, S.; Perumal, S.; Almansour, A. I. Tetrahedron Lett. 2012, 53, 1144.

[35] Wan, J.-P.; Zhou, R. H.; Liu, Y. Y.; Cai, M. Z. RSC Adv. 2013, 3, 2477.

[36] Muthusaravanan, S.; Devi bala, B.; Perumal, S. Tetrahedron Lett. 2013, 54, 5302.

[37] Muthusaravanan, S.; Sasikumar, C.; Devi bala, B.; Perumal, S. Green Chem. 2014, 16, 1297.

[38] Petrow, V. A. J. Chem. Soc. 1946, 888.

[39] Mirza-Aghayan, M.; Langrodi, M. K.; Rahimifard, M.; Boukherroub, R. Appl. Organomet. Chem. 2009, 23, 267.

[40] Yang, J. Y.; Wang, C. Y.; Xie, X.; Li, H.-F.; Li, Y. Z. Eur. J. Org. Chem. 2010, 4189.

[41] Liu, Z. M.; Zhang, L. L.; Sun, J.; Yan, C. G. Chin. J. Chem. 2013, 31, 479.

[42] Sirijindalert, T.; Hansuthirakul, K.; Rashatasakhon, P.; Sukwattanasinitt, M.; Ajavakom, A. Tetrahedron 2010, 66, 5161.

[43] Sasada, T.; Kobayashi, F.; Moriuchi, M.; Sakai, N.; Konakahara, T. Synlett 2011, 2029.

[44] Wan, J.-P.; Liu, Y. Y. Synthesis 2010, 3943.

[45] Wan, J.-P.; Pan, Y.-J. Chem. Commun. 2009, 2768.

[46] Darwish, E. S.; Abdelhamid, I. A.; Nasra, M. A.; Abdel-Gallil, F. M.; Fleita, D. H. Helv. Chim. Acta 2010, 93, 1204.

[47] Chen, Z. G.; Wang, D.; Li, Y. N.; Wang, Y. J.; Hu, J. L.; Xia, W. Acta Chim. Sinica 2012, 70, 2236 (in Chinese).

(陈战国, 王丹, 李亚男, 王英杰, 胡均利, 夏伟, 化学学报, 2012, 70, 2236.)

基于缺电子烯胺交叉氨化过程的多组分反应研究进展

Recent Advances on Multicomponent Reactions Based on the Transamination Process of Electron Deficient Enamines

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