Reviews

Recent Progress on Post-Ugi Reaction

  • Li Xiuming ,
  • Jia Xueshun ,
  • Yin Liang
Expand
  • a Department of Chemistry, Shanghai University, Shanghai 200444;
    b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2017-04-17

  Revised date: 2017-05-19

  Online published: 2017-05-25

Supported by

Project supported by the National Natural Science Foundation of China (No. 21472121).

Abstract

Ugi reaction is an effective and atom-economical multicomponent reaction. The sequences of Ugi multicomponent reactions and following various postcondensation transformations constitute an extremely powerful synthetic method for heterocyclic compounds with elaborate substitution patterns. Herein, the development in this field is summarized.

Cite this article

Li Xiuming , Jia Xueshun , Yin Liang . Recent Progress on Post-Ugi Reaction[J]. Chinese Journal of Organic Chemistry, 2017 , 37(9) : 2237 -2249 . DOI: 10.6023/cjoc201704026

References

[1] Tzitzikas, T. Z.; Chandgude, A. L.; Dömling, A. Chem. Rec. 2015, 15, 981.
[2] Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234.
[3] Zhu, J. P.; Wang, Q.; Wang, M. X. Multicomponent Reaction in Organic Synthesis, Wiley-VCH, Weinheim, 2015.
[4] Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083.
[5] Benjamin, H. R.; Zaretsky, S.; Rai, V.; Yudin, K. A. Chem. Rev. 2014, 114, 8323.
[6] Tang, Z.; Liu, Z.; An, Y.; Jiang, R.; Zhang, X.; Li, C.; Jia. X. J.Org. Chem. 2016, 81, 9158.
[7] Ugi, I.; Meyr, R.; Fetzer, U. Angew. Chem. 1959, 71, 386.
[8] Váradi, A.; Palmer, T. C.; Dardashti, R. N.; Majumdar, S. Molecules 2016, 21, 19.
[9] Hu, H.; Li, A.; Zhang, H.; Shi, D. Chin. J. Org. Chem. 2015, 35, 2162(in Chinese). (胡汉宁, 黎安玲, 张瀚匀, 石德清, 有机化学, 2015, 35, 2162.)
[10] Zhan, Y.; Wang, B.; Zhang, L.; Zhang, Y.; Zhang, X.; Li, Z.; Song, H. Acta Chim. Sinica 2015, 73, 1173(in Chinese). (詹益周, 王宝雷, 张丽媛, 张燕, 张晓, 李正名, 宋海斌, 化学学报, 2015, 73, 1173.)
[11] Xiao, L.; Peng, X.; Zhou, Q.; Kou, W.; Shi, Y. Chin. J. Org. Chem. 2015, 35, 1204(in Chinese). (肖立伟, 彭晓霞, 周秋香, 寇伟, 时亚茹, 有机化学, 2015, 35, 1204.)
[12] Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
[13] Sadjadi, S.; Heravi, M. M.; Nazarib, N. RSC Adv. 2016, 6, 53203.
[14] Haji, M. Beilstein J. Org. Chem. 2016, 12, 1269.
[15] Wang, Y.; Liu, Z.; Tang, C.; Bi, X. J. Mol. Sci. 2016, 32, 1(in Chinese). (王也铭, 刘兆洪, 唐春霖, 毕锡和, 分子科学学报, 2016, 32, 1.)
[16] Zhang, Z.; Zheng, X.; Guo, C. Chin. J. Org. Chem. 2016, 36, 1241(in Chinese). (张钊瑞, 郑晓霖, 郭长彬, 有机化学, 2016, 36, 1241.)
[17] Ugi, I. Angew. Chem. 1961, 74, 9.
[18] Nixey, T.; Kelly, M.; Hulme, C. Tetrahedron Lett. 2000, 41, 8729.
[19] Nixey, T.; Kelly, M.; Semin, D.; Hulme, C. Tetrahedron Lett. 2002, 43, 3681.
[20] Nayak, M.; Batra, S. Tetrahedron Lett. 2010, 51, 510.
[21] Nixey, T.; Kelly, M.; Hulme, C. Tetrahedron Lett. 2000, 41, 8729.
[22] Kalinski, C.; Umkehrer, M.; Gonnard, S.; Jager, N.; Ross, G.; Hillerb, W. Tetrahedron Lett. 2006, 47, 2041.
[23] Yerande, S. G.; Newase, K. M.; Singh, B.; Boltjes, A.; Dömling, A. Tetrahedron Lett. 2014, 55, 3263.
[24] Borisov, R. S.; Polyakov, A. I.; Medvedeva, L. A.; Khrustalev, V. N.; Guranova, N. I.; Voskressensky, L. G. Org. Lett. 2010, 12, 3894.
[25] Shmatova, O. I.; Nenajdenko, V. G. Eur. J. Org. Chem. 2013, 6397.
[26] Shmatova, O. I.; Nenajdenko, V. G. J. Org. Chem. 2013, 78, 9214.
[27] Mikaimi, K.; Lautens, M. New Frontiers in Asymmetric Catalysis, Wiley, New York, 2007.
[28] Ugi, I.; Rosendahl, F. K. Justus Liebigs Ann. Chem. 1963, 666, 65.
[29] Shevchenko, N. E.; Nenajdenko, V. G.; Röschenthaler, G.-V. J. Fluorine Chem. 2008, 129, 390.
[30] Nenajdenko, V. G.; Zakurdaev, E. P.; Prusov, E. V.; Balenkova, E. S. Tetrahedron 2004, 60, 11719.
[31] Kroon, E.; Kurpiewska, K.; Kalinowska-T?us?ik, J.; Dömling, A. Org. Lett. 2016, 18, 4762.
[32] Nutt, R. F.; Joullié, M. M. J. Am. Chem. Soc. 1982, 104, 5852.
[33] Flanagan, D. M.; Joullié, M. M. Synth. Commun. 1989, 19, 1.
[34] Katsuyama, A.; Matsuda, A.; Ichikawa, S. Org. Lett. 2016, 18, 2552
[35] Banfi, L.; Basso, A.; Guanti, G.; Riva, R. Tetrahedron Lett. 2004, 45, 6637.
[36] Hua, D. H.; Miao, S. W.; Bharathi, S. N.; Katsuhira, T.; Bravo, A. A. J. Org. Chem. 1990, 55, 3682.
[37] Golubev, P.; Bakulina, O.; Darin, D.; Krasavin, M. Eur. J. Org. Chem. 2016, 3969.
[38] Morana, F.; Basso, A.; Bella, M.; Riva, R.; Banfi, L. Adv. Synth. Catal. 2012, 354, 2199.
[39] Chapman, T. M.; Davies, I. G.; Gu, B.; Block, T. M.; Scopes, D. I. C.; Hay, P. A.; Courtney, S. M.; McNeill, L. A.; Schofield, C. J.; Davis, B. G. J. Am. Chem. Soc. 2005, 127, 506.
[40] Znabet, A.; Ruijter, E.; de Kanter, F. J. J.; Kohler, V.; Helliwell, M.; Turner, N. J.; Orru, R. V. A. Angew. Chem., Int. Ed. 2010, 49, 5289.
[41] Li, X.-C. Ph.D. Dissertation, Nanjing University, Nanjing, 2011(in Chinese). (刘学超, 博士论文, 南京大学, 南京, 2011.)
[42] Nenajdenko, V. G.; Gulevich, A. V.; Sokolova, N. V.; Mironov, A. V.; Balenkova. E. S. Eur. J. Org. Chem. 2010, 1445.
[43] Vorobyeva, D. V.; Sokolova, N. V.; Nenajdenko, V. G., Peregudov, A. S.; Osipov, S. N. Tetrahedron 2012, 68, 872.
[44] Pramitha, P.; Bahulayan, D. Bioorg. Med. Chem. Lett. 2012, 22, 2598.
[45] Niu, T. F.; Gu, L.; Yi, W. B.; Cai, C. ACS Comb. Sci. 2012, 14, 309.
[46] Shin, S. B. Y.; Yoo, B.; Todaro, L. J.; Kirshenbaum, K. J. Am. Chem. Soc. 2007, 129, 3218.
[47] Pirali, T.; Tron, G. C.; Zhu, J. Org. Lett. 2006, 8, 4145.
[48] Samarasimhareddy, M.; Hemantha, H. P.; Sureshbabu, V. V. Tetrahedron Lett. 2012, 53, 3104.
[49] Salvador, C. E. M.; Pieber, B.; Neu, P. M.; Torvisco, A.; Andrade, C. K. Z.; Kappe, C. O. J. Org. Chem. 2015, 80, 4590.
[50] Xu, Z.; Moliner, F. D.; Cappelli, A. P.; Hulme, C. Angew. Chem., Int. Ed. 2012, 51, 8037.
[51] Xu, Z.; Moliner, F. D.; Cappelli, A. P.; Hulme, C. Org. Lett. 2013, 15, 2738.
[52] Zeng, X.; Wang, H.; Ding, M. Org. Lett. 2015, 17, 2234.
[53] Che, C.; Li, S.; Jiang, X.; Quan, J.; Lin, S.; Yang, Z. Org. Lett. 2010, 20, 4682.
[54] Santra, S.; Andreana, P. R. Angew. Chem., Int. Ed. 2011, 50, 9418.
[55] Santra, S.; Andreana, P. R. J. Org. Chem. 2011, 76, 2261.
[56] Hartung, A.; Seufert, F.; Berges, C.; Gessner. V. H.; Holzgrabe, U. Molecules 2012, 17, 14685.
[57] Yugandhar, D.; Kuriakose, S.; Nanubolu, J. B.; Srivastava, A. K. Org. Lett. 2016, 18, 1040.
[58] Li, Z.; Zhao, Y.; Tian, G.; Yi, H.; Song, G.; Meerveltc, L. V.; Eycken, E. V. V. RSC Adv. 2016, 6, 103601.
[59] Bonnaterre, F.; Bois-Choussy, M.; Zhu, J. Org. Lett. 2006, 19, 4351.
[60] Sharma, N.; Li, Z.; Sharma, U. K.; Van der Eycken, E. V. Org. Lett. 2014, 16, 3884.
[61] Asthana, M.; Sharma, N.; Singh, M. R. Tetrahedron 2014, 70, 7996.
[62] Peshkov, A. A.; Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Tetrahedron 2015, 71, 3863.
[63] He, P.; Nie, Y. B.; Wu, J.; Ding, M. W. Org. Biomol. Chem. 2011, 9, 1429.
[64] Zhong, Y.; Wang, L.; Ding, M.-W. Tetrahedron 2011, 67, 3714.
[65] Duan, Z.; Gao, Y.; Yuan, D.; Ding, M. W. Synlett 2015, 26, 2598.
[66] Beck, B.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2004, 1, 39.
[67] Ramazani, A.; Rezaei, A. Org. Lett. 2010, 12, 2852.
[68] Wang, L.; Ren, Z.; Ding, M. J. Org. Chem. 2015, 80, 641.
[69] Welsch, S. J.; Umkehrer, M.; Kalinski, C.; Ross, G.; Burdack, C.; Kolb, J.; Wild, M.; Ehrlich, A.; Wessjohann, L. A. Tetrahedron Lett. 2015, 56, 1025.
[70] Yan, Y.-M.; Gao, Y.; Ding, M. W. Tetrahedron 2016, 72, 5548.
[71] Furstner, A. Chem. Soc. Rev. 2009, 38, 3208.
[72] Bandini, M.; Bottoni, A.; Chiarucci, M.; Cera, G.; Miscione, G. P. J. Am. Chem. Soc. 2012, 134, 20690.
[73] Vachhani, D. D.; Mehta,V. P.; Modha, S. G.; Van Hecke, K.; Van Meervelt, L.; Van der Eycken, E. V. Adv. Synth. Catal. 2012, 354, 1593.
[74] Kumar, A.; L. Z.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Org. Lett. 2013, 8, 1874.
[75] Bischler, A.; Napieralski, B. Chem. Ber. 1893, 26, 1903.
[76] Ho, G. D.; Seganish, W. M.; Bercovici, A.; Tulshian, D.; Greenlee, W. J.; Van Rijn, R.; Hruza, A.; Xiao, L.; Rindgen, D.; Mullins, D.; Guzzi, M.; Zhang, X.; Bleickardt, C.; Hodgson, R. Bioorg. Med. Chem. Lett. 2012, 22, 2585.
[77] Silvani, A.; Lesma, G.; Crippa, S.; Vece, V. Tetrahedron 2014, 70, 3994.
[78] Hebach, C.; Kazmaier, U. Chem. Commun. 2003, 596.
[79] Banfi, L.; Basso, A.; Giardini, L.; Riva, R.; Rocca, V.; Guanti, G. Eur. J. Org. Chem. 2011, 100.
[80] Shi, J.; Wu, J.; Cui, C.; Dai, W.-M. J.Org. Chem. 2016, 81, 10392.
[81] Banfi, L.; Basso, A.; Guanti, G.; Lecinska, P.; Riva, R. Org. Biomol. Chem. 2006, 4, 4236.
[82] Cheng, G.; He, X.; Tian, L.; Chen, J.; Li, C.; Jia, X.; Li, J. J. Org. Chem. 2015, 80, 11100.
[83] Liu, H.; Domling, A. J. Org. Chem. 2009, 74, 6895.

Outlines

/