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New Applications of Ninhydrin in the Synthesis of Polyheterocyclic Compounds

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Abstract

The review demonstrates new applications of ninhydrin as a versatile reagent in organic synthesis for the preparation of a wide series of polycyclic compounds containing benzofuran, dihydropyrrole, pyrrole, imidazole, pyrimidine, propellane, and other fragments.

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REFERENCES

  1. Ijaj, F., Shafqat, S.S., Ahamd, H.A., Munawar, M.A., and Khan, M.A., J. Heterocycl. Chem., 2019, vol. 56, p. 1231. https://doi.org/10.1002/jhet.3506

    Article  CAS  Google Scholar 

  2. Sahu, K., Banerjee, M., Ghosh, S., Maity, A., Mondal, S., Paira, R., Hazra, A., Karmakar, S., Samanta, A., and Mondal, N., Med. Chem. Res., 2013, vol. 22, p. 2023. https://doi.org/10.1007/s00044-012-0202-z

    Article  CAS  Google Scholar 

  3. Li, X., Yang, L., Peng, C., Xie, X., Leng, H.-J., Wang, B., Tang, Z.-W., He, G., Ouyang, L., Huang, W., and Han, B., Chem. Commun., 2013, vol. 49, p. 8692. https://doi.org/10.1039/c3cc44004

    Article  CAS  Google Scholar 

  4. Yao, W., Liu, Q., Shi, Y., and Tang, J., Heterocycles, 2012, vol. 85, p. 1077. https://doi.org/10.3987/COM-12-12427

    Article  CAS  Google Scholar 

  5. Das, S., RSC Adv., 2020, vol. 10, p. 18875. https://doi.org/10.1039/d0ra02930k

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Korotaev, V., Kutyashev, I., Barkov, A., and Sosnov­skikh, V., Chem. Heterocycl. Compd., 2017, vol. 53, p. 1192. https://doi.org/10.1007/s10593-018-2193-2

    Article  CAS  Google Scholar 

  7. Su, T.L., Lee, T.C., and Kakadiya, R., Eur. J. Med. Chem., 2013, vol. 69, p. 609. https://doi.org/10.1016/j.ejmech.2013.09.016

    Article  CAS  PubMed  Google Scholar 

  8. Kashyap, M., Das, D., Preet, R., Mohapatra, P., Satapathy, S.R., Siddharth, S., Kundu, C.N., and Guchhait, S.K., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 2474. https://doi.org/10.1016/j.bmcl.2012.02.007

    Article  CAS  PubMed  Google Scholar 

  9. Rahimi, F., Hosseini, H., and Bayat, M., Tetrahedron Lett., 2018, vol. 59, p. 818. https://doi.org/10.1016/j.tetlet.2018.01.050

    Article  CAS  Google Scholar 

  10. Rezvanian, A., Moradi, F., Zadsirjan, V., Mohammad­nejad, M., and Heravi, M.M., Mol. Diversity, 2020, vol. 24, p. 1313. https://doi.org/10.1007/s11030-019-09996-7

    Article  CAS  Google Scholar 

  11. Olyaei, A., Taheri, N., and Sadeghpour, M., Res. Chem. Intermed., 2021, vol. 47, p. 1211. https://doi.org/10.1007/s11164-020-04325-2

    Article  CAS  Google Scholar 

  12. Karami, H., Hossaini, Z., Sabbaghan, M., and Rostami-Charati, F., Chem. Heterocycl. Compd., 2018, vol. 54, p. 1040. https://doi.org/10.1007/s10593-018-2388-6

    Article  CAS  Google Scholar 

  13. Kochia, K., Bayat, M., Nasri, S., and Mohammadi, A., Mol. Diversity, 2020, vol. 24, p. 1015. https://doi.org/10.1007/s11030-019-10009-w

    Article  CAS  Google Scholar 

  14. Alizadeh, A., Sanjari, E., Roosta, A., and Hal­vagar, M.R., Mol. Diversity, 2021, vol. 25, p. 2063. https://doi.org/10.1007/s11030-020-10097-z

    Article  CAS  Google Scholar 

  15. Alizadeh, A., Noaparast, Z., Sabahnoo, H., and Zohreh, N., Synlett, 2010, vol. 2010, no. 10, p. 1469. https://doi.org/10.1055/s-0029-1219934

    Article  CAS  Google Scholar 

  16. Mal, K., Naskar, B., Mondal, A., Goswami, S., Prodhan, C., Chaudhuri, K., and Mukhopadhyay, C., Org. Biomol. Chem., 2018, vol. 16, p. 5920. https://doi.org/10.1039/c8ob01411f

    Article  CAS  PubMed  Google Scholar 

  17. Kaur, M., Bhardwaj, M., Sharma, H., Paul, S., and Clark, J.H., New J. Chem., 2017, vol. 41, p. 5521. https://doi.org/10.1039/C7NJ00361G

    Article  Google Scholar 

  18. Moradi, A.V., J. Chem. Res., 2017, vol. 41, p. 403. https://doi.org/10.3184/174751917X14967701767021

    Article  CAS  Google Scholar 

  19. Kalluraya, B., Mallya, S., and Kumar, A.K., J. Hetero­cycl. Chem., 2018, vol. 55, p. 2075. https://doi.org/10.1002/JHET.3247

    Article  CAS  Google Scholar 

  20. Narayanarao, M., Koodlur, L., Gopal, S., Reddy, S.Y., and Kamila, S., Synth. Commun., 2018, vol. 48, p. 2441. https://doi.org/10.1080/00397911.2018.1508722

    Article  CAS  Google Scholar 

  21. Alizadeh, A., Roosta, A., and Halvagar, M., ChemistrySelect, 2019, vol. 4, p. 71. https://doi.org/10.1002/SLCT.201803418

    Article  CAS  Google Scholar 

  22. Nayak, S., Panda, P., Mohapatra, S., Raiguru, B., and Baral, N., J. Heterocycl. Chem., 2019, vol. 56, p. 1757. https://doi.org/10.1002/jhet.3534

    Article  CAS  Google Scholar 

  23. Filatov, A.S., Wang, S., Khoroshilova, O.V., Lozov­skiy, S.V., Larina, A.G., Boitsov, V.M., and Stepa­kov, A.V., J. Org. Chem., 2019, vol. 84, p. 7017. https://doi.org/10.1021/acs.joc.9b00753

    Article  CAS  PubMed  Google Scholar 

  24. Hegde, S.G., Koodlur, L., and Narayanarao, M., Synth. Commun., 2019, vol. 49, p. 3453. https://doi.org/10.1080/00397911.2019.1672746

    Article  CAS  Google Scholar 

  25. Palchykov, V.A., Chabanenko, R.M., Konshin, V.V., Dotsenko, V.V., Krivokolysko, S.G., Chigorina, E.A., Horak, Y.I., Lytvyn, R.Z., Vakhula, A.A., Obu­shak, M.D., and Mazepa, A.V., New J. Chem., 2018, vol. 42, p. 1403. https://doi.org/10.1039/C7NJ03846A

    Article  CAS  Google Scholar 

  26. Deivasigamani, G. and Rajukrishnan, S.B.A., Synth. Commun., 2021, vol. 51, p. 2063. https://doi.org/10.1080/00397911.2021.1919901

    Article  CAS  Google Scholar 

  27. Deivasigamani, G. and Rajukrishnan, S.B.A., Synth. Commun., 2020, vol. 50, p. 3820. https://doi.org/10.1080/00397911.2020.1812081

    Article  CAS  Google Scholar 

  28. Alizadeh, A., Ghasemzadeh, H., Roosta, A., and Halvagar, M.R., ChemistrySelect, 2019, vol. 4, p. 4483. https://doi.org/10.1002/SLCT.201900639

    Article  CAS  Google Scholar 

  29. Mani, K.S., Kaminsky, W., and Rajendran, S.P., New J. Chem., 2018, vol. 42, p. 301. https://doi.org/10.1039/C7NJ02993D

    Article  Google Scholar 

  30. Mani, K.S., Murugesapandian, B., Kaminsky, W., and Rajendran, S.P., Tetrahedron Lett., 2018, vol. 59, p. 2921. https://doi.org/10.1016/j.tetlet.2018.06.035

    Article  CAS  Google Scholar 

  31. Wen, R., Cen, L., Ma, Y., Wang, J., and Zhu, S., Tetrahedron Lett., 2018, vol. 59, p. 1686. https://doi.org/10.1016/j.tetlet.2018.03.059

    Article  CAS  Google Scholar 

  32. Gupta, S. and Khurana, J.M., ChemistrySelect, 2019, vol. 4, p. 7200. https://doi.org/10.1002/slct.201901531

    Article  CAS  Google Scholar 

  33. Reddy, M.S., Chowhan, L.R., Kumar, N.S., Ramesh, P., and Mukkamala, S.B., Tetrahedron Lett., 2018, vol. 59, p. 1366. https://doi.org/10.1016/j.tetlet.2018.02.044

    Article  CAS  Google Scholar 

  34. Arumugan, N., Almansour, A.I., Kumar, R.S., Kotresha, D., Saiswaroop, R., and Venketesh, S., Bioorg. Med. Chem., 2019, vol. 27, p. 2621. https://doi.org/10.1016/j.bmc.2019.03.058

    Article  CAS  Google Scholar 

  35. Singh, R., Bhardwaj, D., and Saini, M.R., RSC Adv., 2021, vol. 11, p. 4760. https://doi.org/10.1039/d0ra09130h

    Article  CAS  Google Scholar 

  36. Shirsat, P.K., Narasimhulu, V., and Kumbhare, R.M., ChemistrySelect, 2019, vol. 4, p. 8550. https://doi.org/10.1002/slct.201901831

    Article  CAS  Google Scholar 

  37. Shirsat, P.K., Khomane, N.B., Meshram, S.H., Sridhar, B., Meshram, H.M., and Kumbhare, R.M., Synthesis, 2019, vol. 51, p. 1473. https://doi.org/10.1055/s-0037-1610999

    Article  CAS  Google Scholar 

  38. Shinde, S.S., Laha, S., Tiwari, D.K., Sridhar, B., and Likhar, P.R., Org. Biomol. Chem., 2019, vol. 17, p. 4121. https://doi.org/10.1039/C9OB00560A

    Article  CAS  PubMed  Google Scholar 

  39. Sathi, V., Deepthi, A., and Thomas, N.V., J. Heterocycl. Chem., 2019, vol. 56, p. 2333. https://doi.org/10.1002/jhet.3619

    Article  CAS  Google Scholar 

  40. Boraei, A.T.A., Arkivoc, 2016, vol. 2016, part (iii), p. 71. https://doi.org/10.3998/ark.5550190.p009.399

    Article  CAS  Google Scholar 

  41. Boraei, A.T.A., Ghabbour, H.A., Sarhan, A.A.M., and Barakat, A., ACS Omega, 2020, vol. 5, p. 5436. https://doi.org/10.1021/acsomega.0c00045

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Debnath, K., Pathak, S., and Pramanik, A., Tetrahedron Lett., 2014, vol. 55, p. 1743. https://doi.org/10.1016/j.tetlet.2014.01.109

    Article  CAS  Google Scholar 

  43. Das, S. and Dutta, A., Heterocycles, 2016, vol. 92, p. 701. https://doi.org/10.3987/COM-15-13385

    Article  CAS  Google Scholar 

  44. Velikorodov, A.V., Stepkina, N.N., Osipova, V.P., Zukhairaeva, A.S., and Shustova, E.A., Russ. J. Org. Chem., 2021, vol. 57, p. 575. https://doi.org/10.1134/S1070428021040114

    Article  CAS  Google Scholar 

  45. Das, S., Dutta, A., Maity, S., Ghosh, P., and Mahali, K., Synlett, 2018, vol. 29, p. 581. https://doi.org/10.1055/s-0036-1589146

    Article  CAS  Google Scholar 

  46. Das, S., Das, P., Maity, S., Ghosh, P., and Dutta, A., J. Mol. Struct., 2020, vol. 1224, article ID 129033. https://doi.org/10.1016/j.molstruc.2020.129033

  47. Malti, S., Roy, N., Thilak Babu, L., Moharana, P., Athira, S.S., Sreedhar, E.D., De, S., Kumar, S.K.A., and Paira, P., New J. Chem., 2020, vol. 44, p. 920. https://doi.org/10.1039/C9NJ03131F

    Article  Google Scholar 

  48. Velikorodov, A.V., Zukhairaeva, A.S., Chabakova, A.K., and Kovalev, V.B., Russ. J. Org. Chem., 2018, vol. 54, p. 1509. https://doi.org/10.1134/S1070428018100123

    Article  CAS  Google Scholar 

  49. Kundu, A., Pathak, S., Debnath, K., and Pramanik, A., Tetrahedron Lett., 2014, vol. 55, p. 3960. https://doi.org/10.1016/j.tetlet.2014.04.027

    Article  CAS  Google Scholar 

  50. Kundu, A. and Pramanik, A., Tetrahedron Lett., 2014, vol. 55, p. 4466. https://doi.org/10.1016/j.tetlet.2014.06.064

    Article  CAS  Google Scholar 

  51. Das, S. and Dutta, A., ChemistrySelect, 2020, vol. 5, p. 11361. https://doi.org/10.1002/slct.202003245

    Article  CAS  Google Scholar 

  52. Sirouspour, M. and Souri, S., J. Heterocycl. Chem., 2016, vol. 53, p. 147. https://doi.org/10.1002/jhet.2283

    Article  CAS  Google Scholar 

  53. Tang, Y.Z., Liu, Y.H., and Chen, J.X., Mini-Rev. Med Chem., 2012, vol. 12, p. 53. https://doi.org/10.2174/138955712798868968

    Article  CAS  PubMed  Google Scholar 

  54. El-Sayed, H.A., Assy, M.G., Mahmoud, W.M., El-Sheakh, A.A., and Morsy, H.A., J. Heterocycl. Chem., 2019, vol. 57, p. 805. https://doi.org/10.1002/jhet.3825

    Article  CAS  Google Scholar 

  55. Huang, J.-M., Yokoyama, R., Yang, C.-S., and Fukuyama, Y., Tetrahedron Lett., 2000, vol. 41, p. 6111. https://doi.org/10.1016/S0040-4039(00)01023-6

    Article  CAS  Google Scholar 

  56. Lobo, G., Monasterios, M., Rodrigues, J., Camboa, N., Capparelli, M.V., Martínez-Cuevas, J., Lein, M., Jung, K., Abramjuk, C., and Charris, J., Eur. J. Med. Chem., 2015, vol. 96, p. 281. https://doi.org/10.1016/j.ejmech.2015.04.023

    Article  CAS  PubMed  Google Scholar 

  57. Gozzi, G.J., Bouaziz, Z., Winter, E., Daflon-Yunes, N., Aichele, D., Nacereddine, A., Marminon, C., Valdameri, G., Zeinyeh, W., Bollacke, A., Guillon, J., Lacoudre, A., Pinaud, N., Cadena, S.M., Jose, J., Le Borgne, M., and Di Pietro, A., J. Med. Chem., 2015, vol. 58, p. 265. https://doi.org/10.1021/jm500943z

    Article  CAS  Google Scholar 

  58. Rostami-Charati, F., Chin. Chem. Lett., 2014, vol. 25, p. 169. https://doi.org/10.1016/j.cclet.2013.09.016

    Article  CAS  Google Scholar 

  59. Azizian, J., Hatamjafari, F., Karimi, A.R., and Shaaban­zadeh, M., Synthesis, 2006, vol. 2006, no. 5, p. 765. https://doi.org/10.1055/s-2006-926327

    Article  CAS  Google Scholar 

  60. Yavari, I., Seyfi, S., Nematpour, M., and Hossaini, Z., Helv. Chim. Acta, 2010, vol. 93, p. 1413. https://doi.org/10.1002/hlca.200900408

    Article  CAS  Google Scholar 

  61. Hemmerling, H.-J. and Reiss, G., Synthesis, 2009, vol. 2009, no. 6, p. 985. https://doi.org/10.1055/s-0028-1087983

    Article  CAS  Google Scholar 

  62. Liu, C.-Z., Han, Y., Qi, W.-J., and Yan, C.-G., Heterocycl. Commun., 2016, vol. 22, p. 301. https://doi.org/10.1515/hc-2016-0123

    Article  CAS  Google Scholar 

  63. Mousavi, S.H., Mohammadizadeh, M.R., Roshan, Z., Jamaleddini, A., and Arimitsu, S., ACS Omega, 2020, vol. 5, p. 18273. https://doi.org/10.1021/acsomega.0c01934

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  64. Yang, C., Schanne, F.A.X., Yoganathan, S., and Stephani, R.A., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 2912. https://doi.org/10.1016/j.bmcl.2016.04.040

    Article  CAS  PubMed  Google Scholar 

  65. Shtamburg, V.G., Shtamburg, V.V., Anishchenko, A.A., Shishkina, S.V., Mazepa, A.V., and Konovalova, I.S., Eur. Chem. Bull., 2020, vol. 95, p. 125. https://doi.org/10.17628/ecb.2020.9.125-131

    Article  CAS  Google Scholar 

  66. Shtamburg, V.G., Shtamburg, V.V., Anishchenko, A.A., Mazepa, A.V., and Rusanov, E.B., J. Mol. Struct., 2021, vol. 1248, article ID 131443. https://doi.org/10.1016/j.molstruc.2021.131443

  67. Shtamburg, V.G., Shtamburg, V.V., Anishchenko, A.A., Rusanov, E.B., and Kravchenko, S.V., J. Chem. Technol., 2021, vol. 29, p. 232. https://doi.org/10.15421/jchemtech.v29i2.231195

    Article  CAS  Google Scholar 

  68. El-Abadelah, M.M., Awwadi, F.F., Abdullah, A.H., and Voelter, W., Z. Naturforsch., Teil B, 2020, vol. 75, p. 559. https://doi.org/10.1515/znb-2020-0027

    Article  CAS  Google Scholar 

  69. Hamed, E.O., Assy, M.G., and Galahom, M.M., Russ. J. Org. Chem., 2020, vol. 56, p. 1062. https://doi.org/10.1134/S1070428020060159

    Article  CAS  Google Scholar 

  70. El-Sayed, H.A., Assy, M.G., Mahmoud, W.M., El-Sheakh, A.A., and Morsy, H.A., Russ. J. Gen. Chem., 2020, vol. 90, p. 148. https://doi.org/10.1134/S1070363220010235

    Article  CAS  Google Scholar 

  71. Mandal, S. and Pramanik, A., Tetrahedron, 2020, vol. 76, article ID 130817. https://doi.org/10.1016/j.tet.2019.130817

  72. Wang, J., Zhang, M.M., and Wang, X.S., Res. Chem. Intermed., 2017, vol. 43, p. 2985. https://doi.org/10.1007/s11164-016-2807-1

    Article  CAS  Google Scholar 

  73. Marthy, V.N., Nikumbh, S.P., Kumar, S.P., Chiranjeevi, Y., Rao, L.V., and Raghunadh, A., Synlett, 2016, vol. 27, p. 2362. https://doi.org/10.1055/s-0035-1562465

    Article  CAS  Google Scholar 

  74. Devi, R.V., Garande, A.M., Maity, D.K., and Bhate, P.M., J. Org. Chem., 2016, vol. 81, p. 1689. https://doi.org/10.1021/acs.joc.5b02327

    Article  CAS  PubMed  Google Scholar 

  75. Dotsenko, V.V., Muraviev, V.S., Lukina, D.Yu., Strelkov, V.D., Aksenov, N.A., Aksenova, I.V., Krapi­vin, G.D., and Dyadyuchenko, L.V., Russ. J. Gen. Chem., 2020, vol. 90, p. 948. https://doi.org/10.1134/S1070363220060043

    Article  CAS  Google Scholar 

  76. Akbarzadeh, P. and Koukabi, N., Appl. Organomet. Chem., 2020, vol. 34, article ID e5746. https://doi.org/10.1002/aoc.5474

  77. Gonzalez-Onate, A. and Quevedo, R., J. Chem. Sci., 2020, vol. 132, article no. 49. https://doi.org/10.1007/s12039-020-1751-1

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Authors and Affiliations

  1. Astrakhan State University, 414000, Astrakhan, Russia

    A. V. Velikorodov, E. N. Kutlalieva & S. B. Nosachev

  2. Astrakhan State Medical University, Ministry of Health of the Russian Federation, 414000, Astrakhan, Russia

    A. V. Velikorodov, A. S. Zukhairaeva, E. N. Kutlalieva & E. A. Shustova

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  1. A. V. Velikorodov
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  2. A. S. Zukhairaeva
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  3. E. N. Kutlalieva
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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 1, pp. 7–37 https://doi.org/10.31857/S0514749223010019.

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Velikorodov, A.V., Zukhairaeva, A.S., Kutlalieva, E.N. et al. New Applications of Ninhydrin in the Synthesis of Polyheterocyclic Compounds. Russ J Org Chem 59, 1–28 (2023). https://doi.org/10.1134/S1070428023010013

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