Synthesis of α-amino carbonyl compounds: a brief review

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Дәйексөз келтіру

Толық мәтін

Аннотация

α-Amino carbonyl compounds are an important class of nitrogen-containing substances. This review highlights their synthesis using various strategies and considers mechanisms of the processes. The strategies are classified into subcategories based on the type of starting materials, chemical reactions and synthetic methods in use. In the literature survey, different types of reactions are discussed like oxidation, reduction, addition, coupling, C–H amination, oxidative cleavage and rearrangement, amidation, multicomponent cascade reaction, etc., for the synthesis of these compounds. Bibliography — 100 references.

Авторлар туралы

Anindita Mukherjee

Chemical Technological Institute, Ural Federal University named after the First President of Russia B. N. Yeltsin

Sachinta Mahato

Department of Chemistry, Visva-Bharati

Dmitrii Kopchuk

Chemical Technological Institute, Ural Federal University named after the First President of Russia B. N. Yeltsin; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences

Email: dkopchuk@mail.ru
Candidate of chemical sciences, Senior Researcher

Sougata Santra

Chemical Technological Institute, Ural Federal University named after the First President of Russia B. N. Yeltsin

Grigory Zyryanov

Chemical Technological Institute, Ural Federal University named after the First President of Russia B. N. Yeltsin; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences

Email: grigoryz@hotmail.com
Doctor of chemical sciences, Associate professor

Adinath Majee

Department of Chemistry, Visva-Bharati

Oleg Chupakhin

Chemical Technological Institute, Ural Federal University named after the First President of Russia B. N. Yeltsin; Department of Chemistry, Visva-Bharati

Email: chupakhin@ios.uran.ru
Doctor of chemical sciences, Professor

Әдебиет тізімі

  1. J.Zhang, Y.Wang, X.Wang, W.Z.Li. J. Org. Chem., 78, 6154 (2013)
  2. T.Yamagishi, S.Muronoi, S.Hikishima, H.Shimeno, S.Soeda, T.Yokomatsu. J. Org. Chem., 74, 6350 (2009)
  3. Y.V.Smirnova, Z.A.Krasnaya. Russ. Chem. Rev., 69, 1021 (2000)
  4. D.E.Frantz, L.Morency, A.Soheili, J.A.Murry, E.J.J.Grabowski, R.D.Tillyer. Org. Lett., 6, 843 (2004)
  5. T.A.Elmaaty, L.W.Castle. Org. Lett., 7, 5529 (2005)
  6. M.G.Unthank, N.Hussain, V.K.Aggarwal. Angew. Chem., 118, 7224 (2006)
  7. L.V.Frolova, N.M.Evdokimov, K.Hayden, I.Malik, S.Rogelj, A.Kornienko, I.V.Magedov. Org. Lett., 13, 1118 (2011)
  8. Z.Q.Wang, M.Hu, X.C.Huang, L.B.Gong, Y.X.Xie, J.H.Li. J. Org. Chem., 77, 8705 (2012)
  9. M.L.Yuan, J.H.Xie, X.H.Yang, Q.L.Zhou. Synthesis, 46, 2910 (2014)
  10. Y.Hu, W.Wu, X.-Q.Dong, X.Zhang. Org. Chem. Front., 4, 1499 (2017)
  11. J.Cao, T.K.Hyster. ACS Catal., 10, 6171 (2020)
  12. M.Sauer, C.Beemelmanns. Chem. Commun., 58, 8990 (2022)
  13. A.E.van der Westhuyzen, L.V.Frolova, A.Kornienko, W.A.L.van Otterlo. The Alkaloids: Chemistry and Biology, 79, 191 (2018)
  14. J.V.Matlock, S.P.Fritz, S.A.Harrison, D.M.Coe, E.M.McGarrigle, V.K.Aggarwal. J. Org. Chem., 79, 10226 (2014)
  15. K.Seipp, L.Geske, T.Opatz. Mar. Drugs, 19, 514 (2021)
  16. Yu.A.Belousov, A.A.Drozdov. Russ. Chem. Rev., 81, 1159 (2012)
  17. T.M.Brunt, A. Poortman, R.J.M. Niesink, W.van den Brink. J. Psychopharmacol., 25, 1543 (2011)
  18. S.R.Khan, R.T.Berendt, C.D.Ellison, A.B.Ciavarella, E.Asafu-Adjaye, M.A.Khan, P.J.Faustino. In Chapter One -- Bupropion Hydrochloride. Vol. 41. (Ed. H.G.Brittain). Profiles of Drug Substances, Excipients and Related Methodology. (Academic Press, 2016). P. 1
  19. E.Erdik. Tetrahedron, 60, 8747 (2004)
  20. J.M.Concellon, H.Rodriguez-Solla. Curr. Org. Chem., 12, 524 (2008)
  21. A.de la Torre, V.Tona, N.Maulide. Angew. Chem., Int. Ed., 56, 12416 (2017)]
  22. L.A.T.Allen, R.C.Raclea, P.Natho, P.J.Parsons. Org. Biomol. Chem., 19, 498 (2021)
  23. S.Lociuro, L.Pellacani, P.A.Tardella. Tetrahedron Lett., 24, 593 (1983)
  24. S.Fioravanti, M.A.Loreto, L.Pellacani, P.A.Tardella. J. Org. Chem., 50, 5365 (1985)
  25. A.Cipollone, M.A.Loreto, L.Pellacani, P.A.Tardella. J. Org. Chem., 52, 2584 (1987)
  26. D.A.Evans, M.M.Fad, M.T.Bilodeau. J. Am. Chem. Soc., 116, 2742 (1994)
  27. B.W.Lim, K.H.Ahn. Synth. Commun., 26, 3407 (1996)
  28. P.Phukan, A.Sudalai. Indian J. Chem., 40B, 515 (2001)
  29. M.Nakanishi, A.Salit, C.Bolm. Adv. Synth. Catal., 350, 1835 (2008)
  30. A.Yoshimura, V.N.Nemykin, V.V.Zhdankin. Chem.-Eur. J., 17, 10538 (2011)
  31. P.Mizar, T.Wirth. Angew. Chem., Int. Ed., 53, 5993 (2014)
  32. I.Ramakrishna, V.Bhajammanavar, S.Mallik, M.Baidya. Org. Lett., 19, 516 (2017)
  33. A.E.Mattson, K.A.Scheidt. Org. Lett., 6, 4363 (2004)
  34. M.Pohl, B.Lingen, M.Muller. Chem.-Eur. J., 8, 5289 (2002)
  35. S.Iwahana, H.Iida, E.Yashima. Chem.-Eur. J., 17, 8009 (2011)
  36. K.Konidaris, A.Daolio, A.Pizzi, P.Scilabra, G.Terraneo, S.Quici, J.S.Murray, P.Politzer, G.Resnati. Crystal Growth Design, 22, 4987 (2022)
  37. X.Lu, J.Zhang, L.Xu, W.Shen, F.Yu, L.Ding, G.Zhong. Org. Lett., 22, 5610 (2020)
  38. L.Wang, P.Cheng, X.Wang, W.Wang, J.Zeng, Y.Liang, O.Reiser. Org. Chem. Front., 6, 3771 (2019)
  39. M.Shimizu, T.Sahara, R.Hayakawa. Chem. Lett., 30, 792 (2001)
  40. K.Surendra, N.S.Krishnaveni, M.A.Reddy, Y.V.D.Nageswar, K.R.Rao. J. Org. Chem., 68, 9119 (2003)
  41. M.S.Reddy, M.Narender, K.R.Rao. Tetrahedron Lett., 46, 1299 (2005)
  42. K.Surendra, N.S.Krishnaveni, K.R.Rao. Tetrahedron Lett., 46, 4111 (2005)
  43. Z.-B.Luo, J.-Y.Wu, X.-L.Hou, L.-X.Dai. Org. Biomol. Chem., 5, 3428 (2007)
  44. X.Zhang, S.S.Li, L.Wang, L.Xu, J.Xiao, Z.J.Liu. Tetrahedron, 72, 8073 (2016)
  45. M.Lekov, S.Tshepelevitsh, A.Heering, P.G. Plieger, R.Vianello, I.Leito. Eur. J. Org. Chem., 2017, 4475 (2017)
  46. R.Kuwano, R.Ikeda, K.Hirasada. Chem. Commun., 51, 7558 (2015)
  47. R.-C.Raclea, P.Natho, L.A.T.Allen, A.J.P.White, P.J.Parsons. J. Org. Chem., 85, 9375 (2020)
  48. A.Villar, C.H.Hovelmann, M.Nieger, K.Muniz. Chem. Commun., 2005, 3304 (2005)
  49. M.H.Shinde, U.A.Kshirsagar. Org. Biomol. Chem., 14, 858 (2016)
  50. Y.Wei, S.Lin, F.Liang. Org. Lett., 14, 4202 (2012)
  51. Y.Wei, F.Liang, X.Zhang. Org. Lett., 15, 5186 (2013)
  52. Y.Wei, S.Lin, F.Liang, J.Zhang. Org. Lett., 15, 852 (2013)
  53. P.K.Prasad, R.N.Reddi, A.Sudalai. Org. Lett., 18, 500 (2016)
  54. Q.Qin, Y.-Y.Han, Y.-Y.Jiao, Y.He, S.Yu. Org. Lett., 19, 2909 (2017)
  55. T.Miura, T.Biyajima, T.Fujii, M.Murakami. J. Am. Chem. Soc., 134, 194 (2011)
  56. M.Akter, K.Rupa, P.Anbarasan. Chem. Rev., 122, 13108 (2022)
  57. H.Dai, S.Yu, W.Cheng, Z.-F.Xu, C.-Y.Li. Chem. Commun., 53, 6417 (2017)
  58. H.H.San, S.-J.Wang, M.Jiang, X.-Y.Tang. Org. Lett., 20, 4672 (2018)
  59. F.Tan, X.Liu, X.Hao, Y.Tang, L.Lin, X.Feng. ACS Catal., 6, 6930 (2016)
  60. Z.-F.Xu, L. Shan, W. Zhang, M.Cen, C.-Y. Li. Org. Chem. Front., 6, 1391 (2019)
  61. H.T.Tang, Y.B.Zhou, Y.Zhu, H.C.Sun, M.Lin, Z.P.Zhan. Chem.-Asian J., 9, 1278 (2014)
  62. N.Takeda, Y.Kobori, K.Okamura, M.Yasui, M.Ueda. Org. Lett., 22, 9740 (2020)
  63. R.Kumar, Q.H.Nguyen, T.-W.Um, S.Shin. Chem. Rec., 22, e202100172 (2022)
  64. A.Kakuuchi, T.Taguchi, Y.Hanzawa. Eur. J. Org. Chem., 2003, 116 (2003)
  65. S.Mahato, S.Santra, G.V.Zyryanov, A.Majee. J. Org. Chem., 84, 3176 (2019)
  66. E.A.Merritt, B.Olofsson. Angew. Chem., Int. Ed., 48, 9052 (2009)
  67. D.L.Mo, L.X.Dai, X.L.Hou. Tetrahedron Lett., 50, 5578 (2009)
  68. G.Deng, J.Luo. Tetrahedron, 69, 5937 (2013)
  69. B.T.V.Srinivas, V.S.Rawat, B.Sreedhar. Adv. Synth. Catal., 357, 3587 (2015)
  70. Z.Zhang, Y.Luo, H.Du, J.Xu, P.Li. Chem. Sci., 10, 5156 (2019)
  71. D.Yadagiri, P.Anbarasan. Chem. Commun., 51, 14203 (2015)
  72. Z.L.Song, C.A.Fan, Y.Q.Tu. Chem. Rev., 111, 7523 (2011)
  73. X.-M.Zhang, B.-S.Li, S.-H.Wang, K.Zhang, F.-M.Zhang, Y.-Q.Tu. Chem. Sci., 12, 9262 (2021)
  74. R.W.Evans, J.R.Zbieg, S.Zhu, W.Li, D.W.C.MacMillan. J. Am. Chem. Soc., 135, 16074 (2013)
  75. R.Jagatheesan, P.Ramesh, S.Sambathkumar. Synth. Commun., 49, 3265 (2019)
  76. A.M.Andrievsky, M.V.Gorelik. Russ. Chem. Rev., 80, 421 (2011)
  77. Y.Lv, Y.Li, T.Xiong, Y.Lu, Q.Liu, Q.Zhang. Chem. Commun., 50, 2367 (2014)
  78. S.Z.Zard. Chem. Soc. Rev., 37, 1603 (2008)
  79. D.I.Bugaenko, A.A.Volkov, A.V.Karchava, M.A.Yurovskaya. Russ. Chem. Rev., 90, 116 (2021)
  80. K.Murakami, G.J.P.Perry, K.Itami. Org. Biomol. Chem., 15, 6071 (2017)
  81. P.F.Kuijpers, I.J.I.van der Vlugt, S.Schneider, B.de Bruin. Chem.-Eur. J., 23, 13819 (2017)
  82. D.Liu, A.Lei. Chem.-Asian J., 10, 806 (2015)
  83. D.I.Bugaenko, A.V.Karchava, M.A.Yurovskaya. Russ. Chem. Rev. 91, RCR5022 (2022)
  84. B.Tan, N.Toda, C.F.Barbas III. Angew. Chem., Int. Ed., 51, 12538 (2012)
  85. W.G.Jia, D.D.Li, Y.C.Dai, H.Zhang, L.Q.Yan, E.H.Sheng, Y.Wei, X.L.Mua, K.W.Huang. Org. Biomol. Chem., 12, 5509 (2014)
  86. Q.Jiang, B.Xu, A.Zhao, J.Jia, T.Liu, C.Guo. J. Org. Chem., 79, 8750 (2014)
  87. V.F.Sardela, A.R.Carvalho, I.K.da C. Nunes. Toxicol. Anal. Clinique, 30, 149 (2018)
  88. S.Liang, C.C.Zeng, H.Y.Tian, B.G.Sun, X.G.Luo, F.Ren. J. Org. Chem., 81, 11565 (2016)
  89. Y.Kumar, Y.Jaiswal, R.Thakur, A.Kumar. ChemistrySelect, 3, 5614 (2018)
  90. K.J.Emery, T.Tuttle, J.A.Murphy. Org. Biomol. Chem., 15, 8810 (2017)
  91. Y.Wang, Y.Du, X.Huang, X.Wu, Y.Zhang, S.Yang, Y.R.Chi. Org. Lett., 19, 632 (2017)
  92. N.Zhang, S.R.Samanta, B.M.Rosen, V.Percec. Chem. Rev., 114, 5848 (2014)
  93. S.Guha, V.Rajeshkumar, S.S.Kotha, G.Sekar. Org. Lett., 17, 406 (2015)
  94. N.Chalmpes, I.Tantis, A.Bakandritsos, A.B.Bourlinos, M.A.Karakassides, D.Gournis. Nanomaterials, 10, 1564 (2020)
  95. L.Lia, Q.Zeng, G.Li, Z.Tang. Synlett, 30, 694 (2019)
  96. Z.Wang. Heyns Rearrangement, in Comprehensive Organic Name Reactions and Reagents. (John Wiley & Sons, Inc, 2010)
  97. X.Xia, B.Chen, X.Zeng, B.Xu. Org. Biomol. Chem., 16, 6918 (2018)
  98. M.M.D.Wilde, M.Gravel. Org. Lett., 16, 5308 (2014)
  99. C.L.Joe, A.G.Doyle. Angew. Chem., Int. Ed., 55, 4040 (2016)
  100. G.-Q.Xu, T.-F.Xiao, G.-X.Feng, C. Liu, B. Zhang, P.-F.Xu. Org. Lett., 23, 2846 (2021)

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