New applications of ninhydrin in the synthesis of polyheterocyclic compounds

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Abstract

The review demonstrates new areas of application of ninhydrin as a universal reagent in organic synthesis for the construction of a wide range of polycyclic compounds with benzofuran, pyrroline, pyrrole, imidazole, pyrimidine, propellanic and other fragments.

About the authors

A. V Velikorodov

Astrakhan State University;Astrakhan State Medical University

Email: avelikorodov@mail.ru

A. S Zukhairaeva

Astrakhan State Medical University

Email: avelikorodov@mail.ru

E. N Kutlalieva

Astrakhan State University;Astrakhan State Medical University

Email: avelikorodov@mail.ru

E. A Shustova

Astrakhan State Medical University

Email: avelikorodov@mail.ru

S. B Nosachev

Astrakhan State University

Email: avelikorodov@mail.ru

References

  1. Ijaj F., Shafqat S.S., Ahamd H.A., Munawar M.A., Khan M.A. J. Heterocycl. Chem. 2019, 56, 1231-1238. doi: 10.1002/jhet.3506
  2. Sahu K., Banerjee M., Ghosh S., Maity A., Mondal S., Paira R., Hazra A., Karmakar S., Samanta A., Mondal N. Med. Chem. Res. 2013, 22, 2023-2037. doi: 10.1007/s00044-012-0202-z
  3. Li X., Yang L., Peng C., Xie X., Leng H.-J., Wang B., Tang Z.-W., He G., Ouyang L., Huang W., Han B. Chem. Commun. 2013, 49, 8692-8694. doi: 10.1039/c3cc44004
  4. Yao W., Liu Q., Shi Y., Tang J. Heterocycles. 2012, 85, 1077-1088. doi: 10.3987/COM-12-12427
  5. Das S. RSC Adv. 2020, 10, 18875-18906. doi: 10.1039/d0ra02930k
  6. Коротаев В., Кутяшев И., Барков А., Сосновских В. ХГС. 2017, 53, 1192-1198.
  7. Korotaev V., Kutyashev I., Barkov A., Sosnovskikh V. Chem. Heterocycl. Compd. 2017, 53, 1192-1198. doi: 10.1007/s10593-018-2193-2
  8. Su T.L., Lee T.C., Kakadiya R. Eur. J. Med. Chem. 2013, 69, 609-621. doi: 10.1016/j.ejmech.2013.09.016
  9. Kashyap M., Das D., Preet R., Mohapatra P., Satapathy S.R., Siddharth S., Kundu C.N., Guchhait S.K. Bioorg. Med. Chem. Lett. 2012, 22, 2474-2479. doi: 10.1016/j.bmcl.2012.02.007
  10. Rahimi F., Hosseini H., Bayat M. Tetrahedron Lett. 2018, 59, 818-822. doi: 10.1016/j.tetlet.2018.01.050
  11. Rezvanian A., Moradi F., Zadsirjan V., Mohammadnejad M., Heravi M.M. Mol. Divers. 2020, 24, 1313-1325. doi: 10.1007/s11030-019-09996-7
  12. Olyaei A., Taheri N., Sadeghpour M. Res. Chem. Intermed. 2021, 47, 1211-1219 doi: 10.1007/s11164-020-04325-2
  13. Karami H., Hossaini Z., Sabbaghan M., Rostami-Charati F. Chem. Heterocycl. Compd. 2018, 54, 1040-1044. doi: 10.1007/s10593-018-2388-6
  14. Kochia K., Bayat M., Nasri S., Mohammadi A. Mol. Divers. 2020, 24, 1015-1024. doi: 10.1007/s11030-019-10009-w
  15. Alizadeh A., Sanjari E., Roosta A., Halvagar M.R. Mol. Divers. 2021, 25, 2063-2072. doi: 10.1007/s11030-020-10097-z
  16. Alizadeh A., Noaparast Z., Sabahnoo H., Zohreh N. Synlett. 2010, 10, 1469-1472. doi: 10.1055/s-0029-1219934
  17. Mal K., Naskar B., Mondal A., Goswami S., Prodhan C., Chaudhuri K., Mukhopadhyay C. Org. Biomol. Chem. 2018, 16, 5920-5931. doi: 10.1039/c8ob01411f
  18. Kaur M., Bhardwaj M., Sharma H., Paul S., Clark J.H. New J. Chem. 2017, 41, 5521-5532. doi: 10.1039/C7NJ00361G
  19. Moradi A.V. J. Chem. Res. 2017, 41, 403-405. doi: 10.3184/174751917X14967701767021
  20. Kalluraya B., Mallya S., Kumar A.K. J. Heterocycl. Chem. 2018, 55, 2075-2081. doi: 10.1002/JHET.3247
  21. Narayanarao M., Koodlur L., Gopal S., Reddy S.Y., Kamila S. Synth. Commun. 2018, 48, 2441-2451. doi: 10.1080/00397911.2018.1508722
  22. Alizadeh A., Roosta A., Halvagar M. ChemistrySelect. 2019, 4, 71-74. doi: 10.1002/SLCT.201803418
  23. Nayak S., Panda P., Mohapatra S., Raiguru B., Baral N. J. Heterocycl. Chem. 2019, 56, 1757-1770. doi: 10.1002/jhet.3534
  24. Filatov A.S., Wang S., Khoroshilova O.V., Lozovskiy S.V., Larina A. G., Boitsov V.M., Stepakov A.V. J. Org. Chem. 2019, 84, 7017-7036. doi: 10.1021/acs.joc.9b00753
  25. Hegde S.G., Koodlur L., Narayanarao M. Synth. Commun. 2019, 49, 3453-3464. doi: 10.1080/00397911.2019.1672746
  26. 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., Mazepa A.V. New J. Chem. 2018, 42, 1403-1412. doi: 10.1039/C7NJ03846A
  27. Deivasigamani G., Rajukrishnan S.B.A. Synth. Commun. 2021, 51, 2063-2076. doi: 10.1080/00397911.2021.1919901
  28. Deivasigamani G., Rajukrishnan S.B.A. Synth. Commun. 2020, 50, 3820-3829. doi: 10.1080/00397911.2020.1812081
  29. Alizadeh A., Ghasemzadeh H., Roosta A., Halvagar M.R. ChemistrySelect. 2019, 4, 4483-4486. doi: 10.1002/SLCT.201900639
  30. Mani K.S., Kaminsky W., Rajendran S.P. New J. Chem. 2018, 42, 301-310. doi: 10.1039/C7NJ02993D
  31. Mani K.S., Murugesapandian B., Kaminsky W., Rajendran S.P. Tetrahedron Lett. 2018, 59, 2921-2929. doi: 10.1016/j.tetlet.2018.06.035
  32. Wen R., Cen L., Ma Y., Wang J., Zhu S. Tetrahedron Lett. 2018, 59, 1686-1690. doi: 10.1016/j.tetlet.2018.03.059
  33. Gupta S., Khurana J.M. ChemistrySelect. 2019, 4, 7200-7203. doi: 10.1002/slct.201901531
  34. Reddy M.S., Chowhan L.R., Kumar N.S., Ramesh P., Mukkamala S.B. Tetrahedron Lett. 2018, 59, 1366-1371. doi: 10.1016/j.tetlet.2018.02.044
  35. Arumugan N., Almansour A.I., Kumar R.S., Kotresha D., Saiswaroop R., Venketesh S. Bioorg. Med. Chem. 2019, 27, 2621-2638. doi: 10.1016/j.bmc.2019.03.058
  36. Singh R., Bhardwaj D., Saini M.R. RSC Adv. 2021, 11, 4760-4804. doi: 10.1039/d0ra09130h
  37. Shirsat P.K., Narasimhulu V., Kumbhare R.M. ChemistrySelect. 2019, 4, 8550-8553. doi: 10.1002/slct.201901831
  38. Shirsat P.K., Khomane N.B., Meshram S.H., Sridhar B., Meshram H.M., Kumbhare R.M. Synthesis. 2019, 51, 1473-1481. doi: 10.1055/s-0037-1610999
  39. Shinde S.S., Laha S., Tiwari D.K., Sridhar B., Likhar P.R. Org. Biomol. Chem. 2019, 17, 4121-4128. doi: 10.1039/C9OB00560A
  40. Sathi V., Deepthi A., Thomas N.V. J. Heterocycl. Chem. 2019, 56, 2333-2340. doi: 10.1002/jhet.3619
  41. Boraei A.T.A. Arkivoc. 2016, 2016, 71-81. doi: 10.3998/ark.5550190.p009.399
  42. Boraei A.T.A., Ghabbour H.A., Sarhan A.A.M., Barakat A. ACS Omega. 2020, 5, 5436-5442. doi: 10.1021/acsomega.0c00045
  43. Debnath K., Pathak S., Pramanik A. Tetrahedron Lett. 2014, 55, 1743-1748. doi: 10.1016/j.tetlet.2014.01.109
  44. Das S., Dutta A. Heterocycles. 2016, 92, 701-707. doi: 10.3987/COM-15-13385
  45. Великородов А.В., Степкина Н.Н., Осипова В.П., Зухайраева А.С., Шустова Е.А. ЖОрХ. 2021, 57, 562-570.
  46. Velikorodov A.V., Stepkina N.N., Osipova V.P., Zukhairaeva A.S., Shustova E.A. Russ. J. Org. Chem. 2021, 57, 575-581. doi: 10.1134/S1070428021040114
  47. Das S., Dutta A., Maity S.,Ghosh P., Mahali K. Synlett. 2018, 29, 581-584. doi: 10.1055/s-0036-1589146
  48. Das S., Das P., Maity S., Ghosh P., Dutta A. J. Mol. Struct. 2020, 1224, 129033. doi: 10.1016/j.molstruc.2020.129033
  49. Malti S., Roy N., Thilak Babu L., Moharana P., Athira S.S., Sreedhar E.D., De S., Kumar S.K.A., Paira P. New J. Chem. 2020, 44, 920-931. doi: 10.1039/C9NJ03131F
  50. Великородов А.В., Зухайраева А.С., Чабакова А.К., Ковалев В.Б. ЖОрХ. 2018, 54, 1497-1502.
  51. Velikorodov A.V., Zukhairaeva A.S., Chabakova A.K., Kovalev V.B. Russ. J. Org. Chem. 2018, 54, 1509-1514. doi: 10.1134/S1070428018100123
  52. Kundu A., Pathak S., Debnath K., Pramanik A. Tetrahedron Lett. 2014, 55, 3960-3968. doi: 10.1016/j.tetlet.2014.04.027
  53. Kundu A., Pramanik A. Terahedron Lett. 2014, 55, 4466-4474. doi: 10.1016/j.tetlet.2014.06.064
  54. Das S., Dutta A. ChemistrySelect. 2020, 5, 11361-11377. doi: 10.1002/slkt.202003245
  55. Sirouspour M., Souri S. J. Heterocycl. Chem. 2016, 53, 147-152. doi: 10.1002/jhet.2283
  56. Tang Y.Z., Liu Y.H., Chen J.X. Mini-Rev Med Chem. 2012, 12, 53-61. doi: 10.2174/138955712798868968
  57. El-Sayed H.A., Assy M.G., Mahmoud W.M., El-Sheakh A.A., Morsy H.A. J. Heterocyclic. Chem. 2019, 57, 1-8. doi: 10.1002/jhet.3825
  58. Huang J.-M., Yokoyama R., Yang C.-S., Fukuyama Y. Tetrahedron Lett. 2000, 41, 6111-6114. doi: 10.1016/S0040-4039(00)01023-6
  59. Lobo G., Monasterios M., Rodrigues J., Camboa N., Capparelli M. V., Martínez-Cuevas J., Lein M., Jung K., Abramjuk C., Charris J. Eur. J. Med. Chem. 2015, 96, 281-295. doi: 10.1016/j.ejmech.2015.04.023
  60. 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., Di Pietro A. J. Med. Chem. 2015, 58, 265-277. doi: 10.1021/jm500943z
  61. Rostami-Charati F. Chin. Chem. Lett. 2014, 25, 169-171. doi: 10.1016/j.cclet.2013.09.016
  62. Azizian J., Hatamjafari F., Karimi A.R., Shaabanzadeh M. Synthesis. 2006, 37, 765-767. doi: 10.1055/s-2006-926327
  63. Yavari I., Seyfi S., Nematpour M., Hossaini Z. Helv. Chim. Acta. 2010, 93, 1413-1417. doi: 10.1002/hlca.200900408
  64. Hemmerling H.-J., Reiss G. Synthesis. 2009, 40, 985-999. doi: 10.1055/s-0028-1087983
  65. Liu C.-Z., Han Y., Qi W.-J., Yan C.-G. Heterocycl. Commun. 2016, 22, 301-306. doi: 10.1515/hc-2016-0123
  66. Mousavi S.H., Mohammadizadeh M.R., Roshan Z., Jamaleddini A., Arimitsu S. ACS Omega. 2020, 5, 18273-18288. doi: 10.1021/acsomega.0c01934
  67. Yang C., Schanne F.A.X., Yoganathan S., Stephani R.A. Bioorg. Med. Chem. Lett. 2016, 26, 2912-2914. doi: 10.1016/j.bmcl.2016.04.040
  68. Shtamburg V.G., Shtamburg V.V., Anishchenko A.A., Shishkina S.V., Mazepa A.V., Konovalova I.S. Eur. Chem. Bull. 2020, 95, 125-131. doi: 10.17628/ecb.2020.125-131
  69. Shtamburg V.G., Shtamburg V.V., Anishchenko A.A., Mazepa A.V., Rusanov E.B. J. Mol. Struct. 2021, 1248, 131443. doi: 10.1016/j.molstruc.2021.131443
  70. Shtamburg V.G., Shtamburg V.V., Anishchenko A.A., Rusanov E.B., Kravchenko S.V. J. Chem. Technol. 2021, 29, 232-239. doi: 10.15421/jchemtech.v29i2.231195
  71. El-Abadelah M.M., Awwadi F.F., Abdullah A.H., Voelter W. Z. Naturforsch. 2020, 75, 559-565. doi: 10.1515/znb.2020-0027
  72. Hamed E.O., Assy M.G., Galahom M.M. Russ. J. Org. Chem. 2020, 56, 1062-1069. doi: 10.1134/S1070428020060159
  73. El-Sayed H.A., Assy M.G., Mahmoud W.M., El-Sheakt A.A., Morsy H.A. Russ. J. Org. Chem. 2020, 90, 148-153. doi: 10.1134/S1070363220010235
  74. Mandal S., Pramanik A. Tetrahedron. 2019, 76, 130817. doi: 10.1016/j.tet.2019.130817
  75. Wang J., Zhang M.M., Wang X.S. Res. Chem. Intermed. 2017, 43, 2985-3005. doi: 10.1007/s11164-016-2807-1
  76. Marthy V.N., Nikumbh S.P., Kumar S.P., Chiranjeevi Y., Rao L.V., Raghunadh A. Synlett. 2016, 27, 2362-2367. doi: 10.1055/s-0035-1562465
  77. Devi R.V., Garande A.M., Maity D.K., Bhate P.M. J. Org. Chem. 2016, 81, 1689-1695. doi: 10.1021/acs.joc.5b02327
  78. Доценко В.В., Муравьев В.С., Лукина Д.Ю., Стрелков В.Д., Аксенов Н.А., Аксенова И.В., Крапивин Г.Д., Дядюченко Л.В. ЖОХ. 2020, 90, 843-847.
  79. Dotsenko V.V., Muraviev V.S., Lukina D.Yu., Strelkov V.D., Aksenov N.A., Aksenova I.V., Krapivin G.D., Dyadyuchenko L.V. Russ. J. Gen. Chem. 2020, 90, 948-960. doi: 10.1134/S1070363220060043
  80. Akbarzadeh P., Koukabi N. Appl. Organometall. Chem. 2020, e5746. doi: 10.1002/aoc.5474
  81. Gonzalez-Onate A., Quevedo R. J. Chem. Sci. 2020, 132, 49. doi: 10.1007/s12039-020-1751-1

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