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Povarov Reaction in the Synthesis of Polycyclic Nitrogen Compounds Containing a Tetrahydroquinoline Fragment

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Abstract

The review analyzes literature data published in the past 8 years on the synthesis of biologically active tetrahydroquinoline derivatives via the Povarov reaction and its three-component modification.

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REFERENCES

  1. Sridharan, V., Suryavanshi, P.A., and Menendez, J.C., Chem. Rev., 2011, vol. 111, p. 7157. https://doi.org/10.1021/cr100307m

    Article  CAS  PubMed  Google Scholar 

  2. Muthukrishnan, I., Sridharan, V., and Menendez, J.C., Chem. Rev., 2019, vol. 119, p. 5057. https://doi.org/10.1021/acs.chemrev.8b00567

    Article  CAS  PubMed  Google Scholar 

  3. Gosmini, R., Nguyen, V.L., Toum, J., Simon, C., Brusq, J.-M.G., Krysa, G., Mirguet, O., Riou-Ey­mard, A.M., Boursier, E.V., Trottet, L., Bamborough, P., Clark, H., Chung, C.-W., Cutler, L., Demont, E.H., Kaur, R., Lewis, A.J., Schilling, M.B., Soden, P.E., Taylor, S., Walker, A.L., Walker, M.D., Prinjha, R.K., and Nicodème, E., J. Med. Chem., 2014, vol. 57, p. 8111. https://doi.org/10.1021/jm5010539

    Article  CAS  PubMed  Google Scholar 

  4. Hanashalshahaby, E.H.A., Unaleroglu, C., Can, A.A.K., Ozgun, A., and Garipcan, B., Turk. J. Chem., 2019, vol. 43, p. 1552. https://doi.org/10.3906/kim-1907-71

    Article  CAS  Google Scholar 

  5. Chen, C., Zingales, S., Wang, T., Yuan, M., Wang, D., Cai, L., and Jiang, Q.J., J. Enzyme Inhib. Med. Chem., 2016, vol. 31, p. 853. https://doi.org/10.3109/14756366.2015.1064120

    Article  CAS  PubMed  Google Scholar 

  6. Dayal, N., Wang, M., and Sintim, H.O., ACS Omega, 2020, vol. 5, p. 23799. https://doi.org/10.1021/acsomega.0c03001

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Chavan, P., Pansare, D.N., Jadhav, S., and Rai, M., Eur. Chem. Bull., 2019, vol. 8, p. 257. https://doi.org/10.17628/ecb.2019.8.257-264

    Article  CAS  Google Scholar 

  8. Kumar, A., Srivastava, S., Gupta, G., Chaturvedi, V., Sinha, S., and Srivastava, R., ACS Comb. Sci., 2011, vol. 13, p. 65. https://doi.org/10.1021/co100022h

    Article  CAS  PubMed  Google Scholar 

  9. Ozaki, T., Sugiyama, R., Shimomura, M., Nishimura, S., Asamizu, S., Katsuyama, Y., Kakeya, H., and Onaka, H., Org. Biomol. Chem., 2019, vol. 17, p. 2370. https://doi.org/10.1039/c8ob02846j

    Article  CAS  PubMed  Google Scholar 

  10. Chander, S., Ashok, P., Zheng, Y.-T., Wang, P., Raja, K.S., Taneja, A., and Murugesan, S., Bioorg. Chem., 2016, vol. 64, p. 66. https://doi.org/10.1016/j.bioorg.2015.12.005

    Article  CAS  PubMed  Google Scholar 

  11. Onyedibe, K.I., Dayal, N., and Sintim, H.O., RSC Med. Chem., 2021, vol. 12, p. 1879. https://doi.org/10.1039/d1md00211b

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Diaz, G., Miranda, I., Sartori, S., Dias, G., Kohlhoff, M., Purgato, G., and Nogueira, M., J. Braz. Chem. Soc., 2018, vol. 29, p. 2646. https://doi.org/10.21577/0103-5053.20180145

    Article  CAS  Google Scholar 

  13. Martínez, S., Pavani, C., Baptista, M., Becerra, M., Quevedo, M., and Ribone, S., J. Biomol. Struct. Dyn., 2019, vol. 38, p. 2412. https://doi.org/10.1080/07391102.2019.1633410

    Article  CAS  PubMed  Google Scholar 

  14. Kimura, T., Suga, T., Kameoka, M., Ueno, M., Inahashi, Y., Matsuo, H., Iwatsuki, M., Shigemura, K., Shiomi, K., Takahashi, Y., Ōmura, S., and Naka­shima, T., J. Antibiot., 2019, vol. 72, p. 169. https://doi.org/10.1038/s41429-018-0117-0

    Article  CAS  Google Scholar 

  15. Povarov, L.S., Russ. Chem. Rev., 1967, vol. 36, p. 656. https://doi.org/10.1070/RC1967v036n09ABEH001680

    Article  Google Scholar 

  16. Glushkov, V.A. and Tolstikov, A.G., Russ. Chem. Rev., 2008, vol. 77, p. 137. https://doi.org/10.1070/RC2008v077n02ABEH003749

    Article  CAS  Google Scholar 

  17. Ghashghaei, O., Masdeu, C., Alonso, C., Palacios, F., and Lavilla, R., Drug Discovery Today, 2018, vol. 29, p. 71. https://doi.org/10.1016/j.ddtec.2018.08.004

    Article  PubMed  Google Scholar 

  18. Huang, Y., Qiu, C., Li, Z., Feng, W., Gan, H., Liu, J., and Guo, K., ACS Sustainable Chem. Eng., 2016, vol. 4, p. 47. https://doi.org/10.1021/acssuschemeng.5b01379

    Article  CAS  Google Scholar 

  19. Das, D.K., Sarkar, S., Khan, A.T., Saravanan, P., and Patra, S., RSC Adv., 2014, vol. 4, p. 3581. https://doi.org/10.1039/C3RA45174G

    Article  CAS  Google Scholar 

  20. Rai, M., Jadhav, S., and Farooqui, M., Orbital: Electron. J. Chem., 2016, vol. 8, p. 149. https://doi.org/10.17807/orbital.v8i3.801

    Article  CAS  Google Scholar 

  21. DaSilva, B.H.S.T., Marana, N.L., Mafud, A.C., and da Silva-Filho, L.C., Struct. Chem., 2014, vol. 25, p. 327. https://doi.org/10.1007/s11224-013-0297-y

    Article  CAS  Google Scholar 

  22. Puligoundla, R.G., Vulupala, H.R., Kommu, N., and Kondra, S.B., Synth. Commun., 2015, vol. 45, p. 494. https://doi.org/10.1080/00397911.2014.956366

    Article  CAS  Google Scholar 

  23. Cimarelli, C., Bordi, S., Piermattei, P., Pellei, M., and Del Bello, F., Synthesis, 2017, vol. 49, p. 5387. https://doi.org/10.1055/S-0036-1589104

    Article  CAS  Google Scholar 

  24. Sokamisa, M.S., Nyondlo, Y.M., and Kinfe, H.H., Arkivoc, 2016, vol. 2016, part (iii), p. 313. https://doi.org/10.3998/ark.5550190.p009.447

    Article  Google Scholar 

  25. Jadhav, S., Farooqui, M., Chavan, P., Hussain, S., and Rai, M., Polycyclic Aromat. Compd., 2022, vol. 42, p. 2067. https://doi.org/10.1080/10406638.2020.1825005

    Article  CAS  Google Scholar 

  26. Rechac, V.L., Cirujano, F.G., Corma, A., and Llabrés, F.X., Eur. J. Inorg. Chem., 2016, vol. 27, p. 4512. https://doi.org/10.1002/ejic.201600372

    Article  CAS  Google Scholar 

  27. Da Silva Abranches, P.A., de Paiva, W.F., de Fátima, A., Martins, F.T., and Fernandes, S.A., J. Org. Chem., 2018, vol. 83, p. 1761. https://doi.org/10.1021/acs.joc.7b02532

    Article  CAS  Google Scholar 

  28. de Paiva, W.F., Braga, I.B., de Assis, J.V., Casta­neda, S.M.B., Sathicq, A.G., Palermo, V., Roma­nelli, G.P., Natalino, R., da Silva, M.J., Martins, F.T., de Carvalho, G.S.G., Amarante, G.W., and Fernandes, S.A., Tetrahedron, 2019, vol. 75, p. 3740. https://doi.org/10.1016/j.tet.2019.05.049

    Article  CAS  Google Scholar 

  29. Rezende, T.R.M., Varejão, J.O.S., de Almeida Sousa, A.L.L., Castañeda, S.M.B., and Fernandes, S.A., Org. Biomol. Chem., 2019, vol. 17, p. 2913. https://doi.org/10.1039/c8ob02928h

    Article  CAS  PubMed  Google Scholar 

  30. Liu, X. and Toy, P.H., Adv. Synth. Catal., 2020, vol. 362, p. 3437. https://doi.org/10.1002/adsc.202000665

    Article  CAS  Google Scholar 

  31. Reyes-Gutiérrez, P.E., Amatov, T.T., Švec, P., Císařo­vá, I., Šaman, D., Pohl, R., Teplý, F., and Pospíšil, L., ChemPlusChem, 2020, vol. 85, p. 2212. https://doi.org/10.1002/cplu.202000151

    Article  CAS  PubMed  Google Scholar 

  32. Li, L.-P., Cai, X., Xiang, Y., Zhang, Y., Song, J., Yang, D.-C., Guan, Z., and He, Y.-H., Green Chem., 2015, vol. 17, p. 3148. https://doi.org/10.1039/C4GC01123F

    Article  CAS  Google Scholar 

  33. Niño, P., Caba, M., Aguilar, N., Terricabras, E., Albericio, F., and Fernández, J.-C., Indian J. Chem., Sect. B, 2016, vol. 55, p. 1384.

    Google Scholar 

  34. Liu, Q., Wang, C., Li, Q., Hou, Y., Wu, Y., Liu, L., Chang, W., and Li, J., J. Org. Chem., 2017, vol. 82, p. 950. https://doi.org/10.1021/acs.joc.6b02496

    Article  CAS  PubMed  Google Scholar 

  35. Chung, P.Y., Tang, J.C.O., Cheng, C.H., Bian, Z.X., Wong, W.Y., Lam, K.H., and Chui, C.H., Springer Plus, 2016, vol. 5, p. 271. https://doi.org/10.1186/s40064-016-1890-5

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. Gurumurthy, Ch., Fatima, N., Reddy, G.N., Kumar, C.G., Sabitha, G., and Ramakrishna, K.V.S., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 5119. https://doi.org/10.1016/j.bmcl.2016.08.017

    Article  CAS  PubMed  Google Scholar 

  37. Moshapo, P.T., Sokamisa, M., Mmutlane, E.M., Mampa, R.M., and Kinfe, H.H., Org. Biomol. Chem., 2016, vol. 14, p. 5627. https://doi.org/10.1039/c5ob02536b

    Article  CAS  PubMed  Google Scholar 

  38. Shushizadeh, M.R., Mostoufi, A., Behfar, A., and Heidary, M., Arab. J. Chem., 2015, vol. 8, p. 868. https://doi.org/10.1016/j.arabjc.2012.06.007

    Article  CAS  Google Scholar 

  39. Yogita, M., Ragini, G., and Ekta, M., Int. J. Res. Chem. Environ., 2015, vol. 5, no. 1, p. 106.

    Google Scholar 

  40. Sanz-Vidal, Á., Miró, J., Sánchez-Roselló, M., del Pozo, C., and Fustero, S., J. Org. Chem., 2016, vol. 81, p. 6515. https://doi.org/10.1021/acs.joc.6b01139

    Article  CAS  PubMed  Google Scholar 

  41. Arai, N. and Ohkuma, T., J. Org. Chem., 2017, vol. 82, p. 7628. https://doi.org/10.1021/acs.joc.7b00838

    Article  CAS  PubMed  Google Scholar 

  42. Basavegowda, N., Mishra, K., Lee, Y.R., and Joh, Y.-G., Bull. Korean Chem. Soc., 2016, vol. 37, p. 142. https://doi.org/10.1002/bkcs/10642

    Article  CAS  Google Scholar 

  43. Jha, A., Chou, T.-Y., AlJaroudi, Z., Ellis, B.D., and Cameron, T.S., Beilstein J. Org. Chem., 2014, vol. 10, p. 848. https://doi.org/10.3762/bjoc.10.81

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. Gatta, F., Giudice, M., Pomponi, M., and Marta, M., Heterocycles, 1992, vol. 34, p. 991. https://doi.org/10.3987/COM-92-5977

    Article  CAS  Google Scholar 

  45. Gutiérrez, M., Arévalo, B., Martínez, G., Valdés, F., Vallejos, G., Carmona, U., and San Martin, A., J. Chem. Pharm. Res., 2015, vol. 7, p. 351.

    Google Scholar 

  46. Duarte, Y., Dueñas, F., and Gutiérrez, M., J. Chem. Pharm. Res., 2015, vol. 7, p. 294.

    CAS  Google Scholar 

  47. Rodríguez, Y., Gutiérrez, M., Ramírez, D., Alzate-Morales, J., Bernal, C.C., Güiza, F.M., and Romero-Bohórquez, A.R., Chem. Biol. Drug Des., 2016, vol. 88, p. 498. https://doi.org/10.1111/cbdd.12773

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. Rodriguez Núnez, Y.A., Norambuena, M., Romero Bohorquez, A.R., Morales-Bayuelo, A., and Gutíer­rez, M., Heliyon, 2019, vol. 5, article ID e02174. https://doi.org/10.1016/j.heliyon.2019.e02174

  49. Castillo, J.-C., Jiménez, E., Portilla, J., Insuasty, B., Quiroga, J., Moreno-Fuquen, R., Kennedy, A.R., and Abonia, R., Tetrahedron, 2018, vol. 74, p. 932. https://doi.org/10.1016/j.tet.2017.12.049

    Article  CAS  Google Scholar 

  50. Kouznetsov, V.V., Merchán-Arenas, D.R., Martínez-Bonilla, C.A., Macías, M.A., Roussel, P., and Gauthier, G.H., J. Braz. Chem. Soc., 2016, vol. 27, p. 2246. https://doi.org/10.5935/0103-5053.20160117

    Article  CAS  Google Scholar 

  51. Bonilla, C.A.M., Galvis, C.E.P., Méndez, L.Y.V, and Kouznetsov, V.V., RSC Adv., 2016, vol. 6, p. 37478. https://doi.org/10.1039/C6RA04325A

    Article  CAS  Google Scholar 

  52. Bianchini, G., Ribelles, P., Becerra, D., Ramos, M.T., and Menéndez, J.C., Org. Chem. Front., 2016, vol. 3, p. 412. https://doi.org/10.1039/C6QO00037A

    Article  CAS  Google Scholar 

  53. Clerigué, J., Ramos, M.T., and Menéndez, J.C., Molecules, 2021, vol. 26, article no. 1330. https://doi.org/10.3390/molecules26051330

  54. Van Miert, S., Hostyn, S., Maes, B.U.W., Cimanga, K., Brun, R., Kaiser, M., Mátyus, P., Dommisse, R., Lemière, G., Vlietinck, A., and Pieters, L., J. Nat. Prod., 2005, vol. 68, p. 674. https://doi.org/10.1021/np0496284

    Article  CAS  PubMed  Google Scholar 

  55. Sundaram, G.S.M., Venkatesh, C., Syam Kumar, U.K., Ila, H., and Junjappa, H., J. Org. Chem., 2004, vol. 69, p. 5760. https://doi.org/10.1021/jo049227t

    Article  CAS  PubMed  Google Scholar 

  56. Pasha, J., Kandagatla, B., Sen, S., Kumar Seerapu, G.P., Bujji, S., Haldar, D., Nanduri, S., and Oruganti, S., Tetrahedron Lett., 2015, vol. 56, p. 2289. https://doi.org/10.1016/j.tetlet.2015.03.078

    Article  CAS  Google Scholar 

  57. Makhanya, T.R., Gengan, R.M., and Ata, A., Synth. Commun., 2019, vol. 49, p. 823. https://doi.org/10.1080/00397911.2019.1573373

    Article  CAS  Google Scholar 

  58. Suzuki, T., Kuwano, S., and Arai, T., Adv. Synth. Catal., 2020, vol. 362, p. 3208. https://doi.org/10.1002/adsc.202000494

    Article  CAS  Google Scholar 

  59. Zanwar, M.R., Gawande, S.D., Kavala, V., Kuo, C.-W., and Yao, C.-F., Adv. Synth. Catal., 2014, vol. 356, p. 3849. https://doi.org/10.1002/adsc.201400424

    Article  CAS  Google Scholar 

  60. Wang, H., Wang, C., Huang, K., Liu, L., Chang, W., and Li, J., Org. Lett., 2016, vol. 18, p. 2367. https://doi.org/10.1021/acs.orglett.6b00804

    Article  CAS  PubMed  Google Scholar 

  61. Cai, J., Li, F., Deng, G.-J., Ji, X., and Huang, H., Green Chem., 2016, vol. 18, p. 3503. https://doi.org/10.1039/C6GC00779A

    Article  CAS  Google Scholar 

  62. Fochi, M., Caruana, L., and Bernardi, L., Synthesis, 2014, vol. 46, p. 135. https://doi.org/10.1055/s-0033-1338581

    Article  CAS  Google Scholar 

  63. Stevanovic, D., Bertuzzi, G., Mazzanti, A., Fochi, M., and Bernardi, L., Adv. Synth. Catal., 2018, vol. 360, p. 893. https://doi.org/10.1002/adsc.201701484

    Article  CAS  Google Scholar 

  64. Huang, D., Xu, F., Chen, T., Wang, Y., and Lin, X., RSC Adv., 2013, vol. 3, p. 573. https://doi.org/10.1039/C2RA22796G

    Article  CAS  Google Scholar 

  65. Yokoi, T., Nakagawa, Y., and Miyagawa, H., Pest Manage. Sci., 2019, vol. 75, p. 115. https://doi.org/10.1002/ps.5160

    Article  CAS  Google Scholar 

  66. Kazancioglu, M.Z., Kalay, E., Kazancioglu, E.A., and Peshkov, V.A., ChemistrySelect, 2019, vol. 4, p. 8797. https://doi.org/10.1002/slct.201902249

    Article  CAS  Google Scholar 

  67. Gelis, C., Levitre, G., Guerineau, V., Touboul, D., Neuville, L., and Masson, G., Eur. J. Org. Chem., 2019, vol. 2019, no. 31, p. 5151. https://doi.org/10.1002/ejoc.201900547

    Article  CAS  Google Scholar 

  68. Guo, Q., Teng, W., Ren, S., Rao, S., Wang, Y., Chen, L., Shen, B., and Takahashi, T., J. Heterocycl. Chem., 2014, vol. 51, p. 1100. https://doi.org/10.1002/jhet.2118

    Article  CAS  Google Scholar 

  69. Bunescu, A., Wang, Q., and Zhu, J., Org. Lett., 2014, vol. 16, p. 1756. https://doi.org/10.1021/ol500447r

    Article  CAS  PubMed  Google Scholar 

  70. Cerra, B., Mostarda, S., Custodi, C., Macchiarulo, A., and Gioiello, A., MedChemComm, 2016, vol. 7, p. 439. https://doi.org/10.1039/C5MD00455A

    Article  CAS  Google Scholar 

  71. Niño, P., Caba, M., Aguilar, N., Terricabras, E., Albericio, F., and Fernàndez, J.-C., Indian J. Chem., Sect. B, 2016, vol. 55, p. 854. http://nopr.niscpr.res.in/handle/123456789/35022

    Google Scholar 

  72. Niño, P., Caba, M., Aguilar, N., Terricabras, E., Albericio, F., and Fernàndez, J.-C., Indian J. Chem., Sect. B, 2016, vol. 55, p. 1117. http://nopr.niscpr.res.in/handle/123456789/35363

    Google Scholar 

  73. Kulkarni, A.R. and Thakur, G.A., Tetrahedron Lett., 2013, vol. 54, p. 6592. https://doi.org/10.1016/j.tetlet.2013.09.107

    Article  CAS  Google Scholar 

  74. Pelit, E. and Turgut, Z., Ultrason. Sonochem., 2014, vol. 21, p. 1600. https://doi.org/10.1016/j.ultsonch.2014.01.009

    Article  CAS  PubMed  Google Scholar 

  75. Olmos, A., Rigolet, S., Louis, B., and Pale, P., J. Phys. Chem. C, 2012, vol. 116, p. 13661. https://doi.org/10.1021/jp303169h

    Article  CAS  Google Scholar 

  76. Baumann, M., React. Chem. Eng., 2019, vol. 4, p. 368. https://doi.org/10.1039/C8RE00217G

    Article  CAS  Google Scholar 

  77. Imrich, H.-G., Conrad, J., Bubrin, D., and Beifuss, U., J. Org. Chem., 2015, vol. 80, p. 2319. https://doi.org/10.1021/jo502882y

    Article  CAS  PubMed  Google Scholar 

  78. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications, Petrov, V.A., Ed., New Jersey: Wiley, 2009. https://doi.org/10.1002/9780470528952

  79. Filler, R. and Saha, R., Future Med. Chem., 2009, vol. 1, p. 777. https://doi.org/10.4155/fmc.09.65

    Article  CAS  PubMed  Google Scholar 

  80. Sharma, P.C., Jain, A., and Jain, S., Acta Pol. Pharm. Drug Res., 2009, vol. 66, p. 587.

    CAS  Google Scholar 

  81. Tolstikov, A.G., Savchenko, R.G., Lukina, E.S., Nedopekin, D.V., Limantceva, R.M., Khalilov, L.M., Mescheryakova, E.S., and Odinokov, V.N., Helv. Chim. Acta, 2014, vol. 97, p. 1317. https://doi.org/10.1002/hlca.201300456

    Article  CAS  Google Scholar 

  82. Tolstikov, A.G., Savchenko, R.G., Lukina, E.S., Nedopekin, D.V., Shakirova, R.M., and Odinokov, V.N., Russ. J. Org. Chem., 2014, vol. 50, p. 128. https://doi.org/10.1134/S1070428014010230

    Article  CAS  Google Scholar 

  83. Savchenko, R.G., Limantseva, R.M., Safarova, I.V., Sharipova, G.M., Meshcheriakova, E.S., Tolstikov, A.G., and Odinokov, V.N., Russ. J. Org. Chem., 2022, vol. 58, p. 226. https://doi.org/10.1134/S1070428022020105

    Article  CAS  Google Scholar 

  84. Tolstikov, A.G., Savchenko, R.G., Lukina, E.S., Limantseva, R.M., and Odinokov, V.N., Russ. Chem. Bull., Int. Ed., 2014, vol. 63, p. 2077. https://doi.org/10.1007/s11172-014-0704-6

    Article  CAS  Google Scholar 

  85. Mellor, J.M., Merriman, G.D., and Riviere, P., Tetra­hedron Lett., 1991, vol. 32, p. 7103. https://doi.org/10.1016/0040-4039(91)85052-7

    Article  CAS  Google Scholar 

  86. Tolstikov, A.G., Savchenko, R.G., Lukina, E.S., Limantseva, R.M., Nedopekin, D.V., Khalilov, L.M., Meshcheriakova, E.S., and Odinokov, V.N., Synthesis, 2015, vol. 47, p. 2467. https://doi.org/10.1055/s-0034-1380696

    Article  CAS  Google Scholar 

  87. Savchenko, R.G., Limantceva, R.M., Khursan, S.L., Me­sheriakova, E.S., Tolstikov, A.G., and Odinokov, V.N., J. Heterocycl. Chem., 2022, vol. 59, p. 2025. https://doi.org/10.1002/jhet.4540

    Article  CAS  Google Scholar 

  88. Benmeddah, A., Bar, N., Villemin, D., Lohier, J.-F., Mostefa-Kara, B., and Legay, R., Helv. Chim. Acta, 2018, vol. 101, article ID e1800023. https://doi.org/10.1002/HLCA.201800023

  89. Stepakov, A.V., Boitsov, V.M., Larina, A.G., and Molchanov, A.P., Russ. J. Org. Chem., 2014, vol. 50, p. 389. https://doi.org/10.1134/S1070428014030154

    Article  CAS  Google Scholar 

  90. Saranya, S., Baiju, T.V., Gopalan, G., and Radha­krishnan, K.V., Synth. Commun., 2018, vol. 48, p. 816. https://doi.org/10.1080/00397911.2018.1427270

    Article  CAS  Google Scholar 

  91. Priestley, E.S., De Lucca, I., Zhou, J., Saiah, E., Stanton, R., Robinson, L., Luettgen, J.M., Wei, A., Wen, X., Knabb, R.M., Wong, P.C., and Wexler, R.R., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 2432. https://doi.org/10.1016/j.bmcl.2013.02.013

    Article  CAS  PubMed  Google Scholar 

  92. Alonso, C., Fuertes, M., González, M., Rubiales, G., Tesauro, C., Knudsen, B.R., and Palacios, F., Eur. J. Med. Chem., 2016, vol. 115, p. 179. https://doi.org/10.1016/j.ejmech.2016.03.031

    Article  CAS  PubMed  Google Scholar 

  93. Mohinuddin, P.Md.K., Dada, R., Almansour, A.I., Arumugam, N., and Yaragorla, S., Tetrahedron Lett., 2019, vol. 60, p. 1043. https://doi.org/10.1016/j.tetlet.2019.03.021

    Article  CAS  Google Scholar 

  94. Arenas, D.R.M. and Kouznetsov, V.V., J. Org. Chem., 2014, vol. 79, p. 5327. https://doi.org/10.1021/jo500516c

    Article  CAS  Google Scholar 

  95. Merchan-Arenas, D.R., Sojo, F., Arvelo, F., and Kouznetsov, V.V., RSC Adv., 2020, vol. 10, p. 42287. https://doi.org/10.1039/d0ra04555a

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  96. Kouznetsov, V.V., Merchán-Arenas, D., Tangarife-Castaño, V., Correa-Royero, J., and Betancur-Galvis, L., Med. Chem. Res., 2016, vol. 25, p. 429. https://doi.org/10.1007/s00044-015-1486-6

    Article  CAS  Google Scholar 

  97. Nair, P.P.S., Chandrashekarappa, K.K.H., Masa­galli, J.N., Nagaraja, P., and Mahadevan, K.M., Int. J. Pharm. Pharm. Sci., 2015, vol. 7, p. 448.

    CAS  Google Scholar 

  98. Forero, J.S.B., de Carvalho, E.M., Jones, J., Jr., and da Silva, F.M., Curr. Org. Synth., 2015, vol. 12, p. 102. https://doi.org/10.2174/1570179411666140722175810

    Article  CAS  Google Scholar 

  99. Romero-Bohórquez, A.R., Kouznetsov, V.V., and Zacchino, S.A., Univ. Sci. (Pontif. Univ. Javeriana, Fac. Cienc.), 2014, vol. 20, p. 177. https://doi.org/10.11144/Javeriana.SC20-2.siea

    Article  Google Scholar 

  100. Bohórquez, A.R.R., Romero-Daza, J., and Acelas, M., Synth. Commun., 2016, vol. 46, p. 338. https://doi.org/10.1080/00397911.2015.1136646

    Article  CAS  Google Scholar 

  101. Tan, Y.-J., Zhang, Z., Wang, F.-J., Wu, H.-H., and Li, Q.-H., RSC Adv., 2014, vol. 4, p. 35635. https://doi.org/10.1039/C4RA05252H

    Article  CAS  Google Scholar 

  102. Kaboudin, B., Sohrabi, M., and Kazemi, F., J. Hetero­cycl. Chem., 2021, vol. 58, p. 1594. https://doi.org/10.1002/jhet.4283

    Article  CAS  Google Scholar 

  103. Alonso, C., Martin-Encinas, E., Rubiales, G., and Pala­cios, F., Eur. J. Org. Chem., 2017, vol. 2017, p. 2916. https://doi.org/10.1002/ejoc.201700258

    Article  CAS  Google Scholar 

  104. Huang, L., Chen, J.-P., Jin, C., and Su, W.-K., Chin. Chem. Lett., 2013, vol. 24, p. 347. https://doi.org/10.1016/j.cclet.2013.01.045

    Article  CAS  Google Scholar 

  105. Yin, D.H., Liu, W., Wang, Z.X., Huang, X., Zhang, J., and Huang, D.C., Chin. Chem. Lett., 2017, vol. 28, p. 153. https://doi.org/10.1016/j.cclet.2016.10.015

    Article  CAS  Google Scholar 

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Funding

The review was written in the framework of state assignment no. FRMS-2022-0081.

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  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 450075, Ufa, Russia

    R. M. Limantseva, R. G. Savchenko, V. N. Odinokov & A. G. Tolstikov

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  1. R. M. Limantseva
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  2. R. G. Savchenko
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  3. V. N. Odinokov
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  4. A. G. Tolstikov
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Correspondence to R. M. Limantseva.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 7, pp. 858–894 https://doi.org/10.31857/S0514749223070029.

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Limantseva, R.M., Savchenko, R.G., Odinokov, V.N. et al. Povarov Reaction in the Synthesis of Polycyclic Nitrogen Compounds Containing a Tetrahydroquinoline Fragment. Russ J Org Chem 59, 1102–1135 (2023). https://doi.org/10.1134/S1070428023070023

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