Nucleophilic substitution of hydrogen in pyridine and its derivatives by organophosphorus nucleophiles in the presence of electron-deficient acetylenes

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The review considers publications on a new easy functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine, phenanthridine) by the electron-deficient acetylene (esters of acetylenecarboxylic acids, acylacetylenes, cyanoacetylenes)/P-nucleophile (phosphine chalcogenides, H -phosphonates) system. Particular attention is paid to the SN H reaction of regioselective cross-coupling of pyridines with secondary phosphine chalcogenides, initiated by acylacetylenes and leading to the formation of 4-chalcogenophosphorylpyridines. In these processes, acetylenes act as trimodal adjuvants by (1) activating the pyridine ring towards P-nucleophiles, (2) deprotonating the P-H bond, and (3) facilitating the nucleophilic addition of the P-centered anion to the heterocyclic fragment, followed by the release of selectively reduced (to E -alkenes) acetylenes.

About the authors

A. A Telezhkin

A.E. Favorskii Irkutsk institute of chemistry SB RAS

P. A Volkov

A.E. Favorskii Irkutsk institute of chemistry SB RAS

Email: volkov_p_a@irioch.irk.ru

K. O Khrapova

A.E. Favorskii Irkutsk institute of chemistry SB RAS

References

  1. Lam K.H., Gambari R., Chun M., Yuen W., Kan C.W., Chan P., Xu L., Tang W., Chui C.H., Cheng G.Y.M. Bioorg. Med. Chem. Lett. 2009, 19, 2266-2269. doi: 10.1016/j.bmcl.2009.02.091
  2. Reddy G.S., Rao K.U.M., Sudha S.S., Reddy N.B., Sundar C.S., Raju C.N., Reddy C.S. Org. Commun. 2013, 6, 41-46.
  3. Dziuganowska Z.A., Ślepokura K., Volle J.-N., Virieux D., Pirat J.-L., Kafarski P. J. Org. Chem. 2016, 81, 4947-4954. doi: 10.1021/acs.joc.6b00220
  4. Gama N.H., Elkhadir A.Y.F., Gordhan B.G., Kana B.D., Darkwa J., Meyer D. Biometals. 2016, 29, 637-650. doi: 10.1007/s10534-016-9940-6
  5. Fereidoonnezhad M., Niazi M., Ahmadipour Z., Mirzaee T., Faghih Z., Faghih Z., Shahsavari H.R. Eur. J. Inorg. Chem. 2017, 2017, 2247-2254. doi: 10.1002/ejic.201601521
  6. Ssemaganda A., Low L.M., Verhoeft K.R., Wambuzi M., Kawoozo B., Nabasumba S.B., Mpendo J., Bagaya B.S., Kiwanuka N., Stanisic D.I. Metallomics. 2018, 10, 444-454. doi: 10.1039/C7MT00311K
  7. Kuchar J., Rust J., Lehmann C.W., Mohr F. Inorg. Chem. 2020, 59, 10557-10568. doi: 10.1021/acs.inorgchem.0c00982
  8. Khin C., Hashmi A.S.K., Rominger F. Eur. J. Inorg. Chem. 2010, 2010, 1063-1069. doi: 10.1002/ejic.200900964
  9. Kumar P., Singh A.K., Pandey R., Pandey D.S. J. Organomet. Chem. 2011, 696, 3454-3464. doi: 10.1016/j.jorganchem.2011.06.031
  10. Yang Y., Gurnham J., Liu B., Duchateau R., Gambarotta S., Korobkov I. Organometallics. 2014, 33, 5749-5757. doi: 10.1021/om5003683
  11. Ren W., Sun F., Chu J., Shi Y. Org. Lett. 2020, 22, 1868-1873. doi: 10.1021/acs.orglett.0c00168
  12. Zhang T., Qin Y., Wu D., Zhou R., Yi X., Liu C. Synth. Commun. 2005, 35, 1889-1895. doi: 10.1081/SCC-200064921
  13. Denton R.M., An J., Adeniran B., Blake A.J., Lewis W., Poulton A.M. J. Org. Chem. 2011, 76, 6749-6767. doi: 10.1021/jo201085r
  14. Alcarazo M., Suárez R.M., Goddard R., Fürstner A. Chem. Eur. J. 2010, 16, 9746-9749. doi: 10.1002/chem.201001779
  15. Wassenaar J., Detz R.J., de Boer S.Y., Lutz M., van Maarseveen J.H., Hiemstra H., Reek J.N.H. J. Org. Chem. 2015, 80, 3634-3642. doi: 10.1021/acs.joc.5b00438
  16. Makosza M., Wojciechowski K. Chem. Rev. 2004, 104, 2631-2666. doi: 10.1021/cr020086+
  17. Gulevskaya A.V., Pozharskii A.F. Adv. Heterocycl. Chem. 2007, 93, 57-115. doi: 10.1016/S0065-2725(06)93002-5
  18. Charushin V.N., Chupakhin O.N. Mendeleev Commun. 2007, 17, 249-254. doi: 10.1016/j.mencom.2007.09.001
  19. Metal Free C-H Functionalization of Aromatics. In Top. Heterocycl. Chem. Eds. V.N. Charushin, O.N. Chupakhin. Cham: Springer Int. Publ. 2014, 37, 1-283. doi: 10.1007/978-3-319-07019-3
  20. Chupakhin O.N., Charushin V.N. Tetrahedron Lett. 2016, 57, 2665-2672. doi: 10.1016/j.tetlet.2016.04.084
  21. Chupakhin O.N., Charushin V.N. Pure Appl. Chem. 2017, 89, 1195-1208. doi: 10.1515/pac-2017-0108
  22. Makosza M. Chem. Eur. J. 2020, 26, 15346-15353. doi: 10.1002/chem.202003770
  23. Chupakhin O.N., Shchepochkin A.V., Charushin V.N. Adv. Heterocycl. Chem. 2020, 131, 1-47. doi: 10.1016/bs.aihch.2019.11.002
  24. Akulov A.A., Varaksin M.V., Mampuys P., Charushin V.N., Chupakhin O.N., Maes B.U.W. Org. Biomol. Chem. 2021, 19, 297-312. doi: 10.1039/D0OB01580F
  25. Makosza M., Jawdosiuk M. J. Chem. Soc. D. 1970, 648-649. doi: 10.1039/C29700000648
  26. Makosza M., Golinski J. Angew. Chem. Int. Ed. 1982, 21, 451-452. doi: 10.1002/anie.198204511
  27. Makosza M., Paszewski M., Sulikowski D. Synlett. 2008, 2008, 2938-2940. doi: 10.1055/s-0028-1087354
  28. Makosza M., Sulikowski D. J. Org. Chem. 2009, 74, 3827-3832. doi: 10.1021/jo900204e
  29. Чупахин О.Н., Трофимов В.А., Пушкарева З.В. ХГС. 1969, 5, 954-955.
  30. Chupakhin O.N., Trofimov V.A., Pushkareva Z.V. Chem. Heterocycl. Compd. 1969, 5, 713. doi: 10.1007/BF00957405
  31. Трофимов В.А., Чупахин О.Н., Пушкарева З.В., Русинов В.Л. ХГС. 1971, 7, 112-114.
  32. Trofimov V.A., Chupakhin O.N., Pushkareva Z.V., Rusinov V.L. Chem. Heterocycl. Compd. 1971, 7, 104-106. doi: 10.1007/BF00477961
  33. Чупахин О.Н., Постовский И.Я. Усп. хим. 1976, 45, 908-937.
  34. Chupakhin O.N., Postovskii I.Ya. Russ. Chem. Rev. 1976, 45, 454-468. doi: 10.1070/RC1976v045n05ABEH002670
  35. Чупахин О.Н., Щепочкин А.В., Чарушин В.Н., Майорова А.В., Куликова Т.В., Шуняев К.Ю., Еняшин А.Н., Слепухин П.А., Суворова А.И. ХГС. 2019, 55, 956-963.
  36. Chupakhin O.N., Shchepochkin A.V., Charushin V.N., Maiorova A.V., Kulikova T.V., Shunyaev K.Yu., Enyashin A.N., Slepukhin P.A., Suvorova A.I. Chem. Heterocycl. Compd. 2019, 55, 956-963. doi: 10.1007/s10593-019-02562-x
  37. Motoyoshiya J., Tsuboi S., Kokin K., Takaguchi Y., Hayashi S., Aoyama H. Heterocycl. Commun. 1998, 4, 25-30. doi: 10.1515/HC.1998.4.1.25
  38. Motoyoshiya J., Ikeda T., Tsuboi S., Kusaura T., Takeuchi Y., Hayashi S., Yoshioka S., Takaguchi Y., Aoyama H. J. Org. Chem. 2003, 68, 5950-5955. doi: 10.1021/jo030046l
  39. De Blieck A., Masschelein K.G.R., Dhaene F., Rozycka-Sokolowska E., Marciniak B., Drabowicz J., Stevens C.V. Chem. Commun. 2010, 46, 258-260. doi: 10.1039/B906808B
  40. De Blieck A., Catak S., Debrouwer W., Drabowicz J., Hemelsoet K., Verstraelen T., Waroquier M., Van Speybroeck V., Stevens C.V. Eur. J. Org. Chem. 2013, 2013, 1058-1067. doi: 10.1002/ejoc.201201437
  41. Trofimov B.A., Volkov P.A., Khrapova K.O., Telezhkin A.A., Ivanova N.I., Albanov A.I., Gusarova N.K., Chupakhin O.N. Chem. Commun. 2018, 54, 3371-3374. doi: 10.1039/C8CC01155A
  42. Volkov P.A., Ivanova N.I., Khrapova K.O., Telezhkin A.A., Borodina T.N., Gusarova N.K., Trofimov B.A. Mendeleev Commun. 2018, 28, 582-583. doi: 10.1016/j.mencom.2018.11.005
  43. Volkov P.A., Telezhkin A.A., Khrapova K.O., Ivanova N.I., Albanov A.I., Gusarova N.K., Trofimov B.A. New J. Chem. 2021, 45, 6206-6219. doi: 10.1039/D1NJ00245G
  44. Volkov P.A., Gusarova N.K., Khrapova K.O., Telezhkin A.A., Albanov A.I., Vasilevskiy S.F., Trofimov B.А. Mendeleev Commun. 2021, 31, 670-672. doi: 10.1016/j.mencom.2021.09.026
  45. Трофимов Б.А., Арбузова С.Н., Гусарова Н.К. Усп. хим. 1999, 68, 240-253.
  46. Trofimov B.A., Arbuzova S.N., Gusarova N.K. Russ. Chem. Rev. 1999, 68, 215-227. doi: 10.1070/RC1999v068n03ABEH000464
  47. Trofimov B.A., Gusarova N.K. Mendeleev Commun. 2009, 19, 295-302. doi: 10.1016/j.mencom.2009.11.001
  48. Gusarova N.K., Arbuzova S.N., Trofimov B.A. Pure Appl. Chem. 2012, 84, 439-459. doi: 10.1351/PAC-CON-11-07-11
  49. Гусарова Н.К., Трофимов Б.А. Усп. хим. 2020, 89, 225-249.
  50. Gusarova N.K., Trofimov B.A. Russ. Chem. Rev. 2020, 89, 225-249. doi: 10.1070/RCR4903
  51. Gusarova N.K., Volkov P.A., Ivanova N.I., Arbuzova S.N., Khrapova K.O., Albanov A.I., Smirnov V.I., Borodina T.N., Trofimov B.A. Tetrahedron Lett. 2015, 56, 4804-4806. doi: 10.1016/j.tetlet.2015.06.062
  52. Гусарова Н.К., Волков П.А., Иванова Н.И., Храпова К.О., Албанов А.И., Трофимов Б.А. ЖОХ. 2016, 86, 538-541.
  53. Gusarova N.K., Volkov P.A., Ivanova N.I., Khrapova K.O., Albanov A.I., Trofimov B.A. Russ. J. Gen. Chem. 2016, 86, 731-734. doi: 10.1134/S1070363216030373
  54. Gusarova N.K., Volkov P.A., Ivanova N.I., Khrapova K.O., Telezhkin A.A., Albanov A.I., Trofimov B.A. Mendeleev Commun. 2017, 27, 553-555. doi: 10.1016/j.mencom.2017.11.004
  55. Волков П.А., Тележкин А.А., Иванова Н.И., Храпова К.О., Албанов А.И., Гусарова Н.К., Трофимов Б.А. ЖОХ. 2018, 88, 769-775.
  56. Volkov P.A., Telezhkin A.A., Ivanova N.I., Khrapova K.O., Albanov A.I., Gusarova N.K., Trofimov B.A. Russ. J. Gen. Chem. 2018, 88, 912-918. doi: 10.1134/S1070363218050122
  57. Волков П.А., Иванова Н.И., Храпова К.О., Албанов А.И., Арбузова С.Н., Гусарова Н.К., Трофимов Б.А. ЖОХ. 2015, 85, 1391-1394.
  58. Volkov P.A., Ivanova N.I., Khrapova K.O., Albanov A.I., Arbuzova S.N., Gusarova N.K., Trofimov B.A. Russ. J. Gen. Chem. 2015, 85, 1978-1981. doi: 10.1134/S1070363215080319
  59. Semenzin D., Etemad-Moghadam G., Albouy D., Diallo O., Koenig M. J. Org. Chem. 1997, 62, 2414-2422. doi: 10.1021/jo9622441
  60. Kumar R.S., Idhayadhulla A., Nasser A.J.A., Selvin J. Eur. J. Med. Chem. 2011, 46, 804-810. doi: 10.1016/j.ejmech.2010.12.006
  61. Prasanthi G., Prasad K.V.S.R.G., Bharathi K. Eur. J. Med. Chem. 2014, 73, 97-104. doi: 10.1016/j.ejmech.2013.12.001
  62. Abbas H.-A.S., El Sayed W.A., Fathy N.M. Eur. J. Med. Chem. 2010, 45, 973-982. doi: 10.1016/j.ejmech.2009.11.039
  63. Fassihi A., Azadpour Z., Delbari N., Saghaie L., Memarian H.R., Sabet R., Alborzi A., Miri R., Pourabbas B., Mardaneh J. Eur. J. Med. Chem. 2009, 44, 3253-3258. doi: 10.1016/j.ejmech.2009.03.027
  64. Salazar T., Gonzalez A., Bandyopadhyay D. J. Anal. Pharm. Res. 2017, 5, 00148. doi: 10.15406/japlr.2017.05.00148
  65. Albouy D., Laspéras M., Etemad-Moghadam G., Koenig M. Tetrahedron Lett. 1999, 40, 2311-2314. doi: 10.1016/S0040-4039(99)00189-6
  66. Shaabani A., Sarvary A., Mousavi-Faraz S., Ng S.W. Monatsh. Chem. 2012, 143, 1061-1065. doi: 10.1007/s00706-011-0686-0
  67. Trofimov B.A., Andriyankova L.V., Shaikhudinova S.I., Kazantseva T.I., Mal'kina A.G., Zhivet'ev S.A., Afonin A.V. Synthesis 2002, 2002, 853-855. doi: 10.1055/s-2002-28516
  68. Shaabani A., Rezayan A.H., Sarvary A., Khavasi H.R. Tetrahedron Lett. 2008, 49, 1469-1472. doi: 10.1016/j.tetlet.2008.01.006
  69. Asghari S., Habibi A.K. Tetrahedron. 2012, 68, 8890-8898. doi: 10.1016/j.tet.2012.08.038
  70. Adib M., Yavari H., Mollahosseini M. Tetrahedron Lett. 2004, 45, 1803-1805. doi: 10.1016/j.tetlet.2003.12.082
  71. Rezayan A.H., Sabahi H., Rahmati A., Maleki A., Kheirjou S. Monatsh. Chem. 2013, 144, 1051-1055. doi: 10.1007/s00706-012-0919-x
  72. Charati F.R., Hossaini Z., Hosseini-Tabatabaei M.R. J. Heterocycl. Chem. 2012, 49, 154-160. doi: 10.1002/jhet.738
  73. Волков П.А., Тележкин А.А., Храпова К.О., Иванова Н.И., Албанов А.И., Апарцин К.А., Гусарова Н.К., Трофимов Б.А. ЖОХ. 2017, 87, 2091-2093.
  74. Volkov P.A., Telezhkin A.A., Khrapova K.O., Ivanova N.I., Albanov A.I., Apartsin K.A., Gusarova N.K., Trofimov B.A. Russ. J. Gen. Chem. 2017, 87, 2902-2903. doi: 10.1134/S1070363217120271
  75. Volkov P.A., Gusarova N.K., Khrapova K.O., Telezhkin A.A., Ivanova N.I., Albanov A.I., Trofimov B.A. J. Organomet. Chem. 2018, 867, 79-85. doi: 10.1016/j.jorganchem.2017.09.031
  76. Arbuzova S.N., Gusarova N.K., Kazantseva T.I., Verkhoturova S.I., Albanov A.I., Afonin A.V., Trofimov B.A. Tetrahedron Lett. 2016, 57, 3515-3517. doi: 10.1016/j.tetlet.2016.06.105
  77. Arbuzova S.N., Gusarova N.K., Kazantseva T.I., Verkhoturova S.I., Albanov A.I., Trofimov B.A. J. Fluor. Chem. 2018, 210, 137-141. doi: 10.1016/j.jfluchem.2018.03.013
  78. Волков П.А., Храпова К.О., Тележкин А.А., Албанов А.И., Апарцин К.А., Трофимов Б.А. ЖОХ. 2022, 92, 1471-1479.
  79. Volkov P.A., Khrapova K.O., Telezhkin A.A., Albanov A.I., Apartsin K.A., Trofimov B.A. Russ. J. Gen. Chem. 2022, 92, 1712-1719. doi: 10.1134/S1070363222090134
  80. Trofimov B.A., Volkov P.A., Khrapova K.O., Telezhkin A.A., Ivanova N.I., Albanov A.I., Gusarova N.K., Belogolova A.M., Trofimov A.B. J. Org. Chem. 2019, 84, 6244-6257. doi: 10.1021/acs.joc.9b00519
  81. Gusarova N.K., Volkov P.A., Ivanova N.I., Khrapova K.O., Albanov A.I., Afonin A.V., Borodina T.N., Trofimov B.A. Tetrahedron Lett. 2016, 57, 3776-3780. doi: 10.1016/j.tetlet.2016.07.024
  82. Yavari I., Mirzaei A., Moradi L. Synth. Commun. 2010, 40, 2407-2414. doi: 10.1080/00397910903249598
  83. Волков П.А., Тележкин А.А., Иванова Н.И., Храпова К.О., Албанов А.И., Гусарова Н.К., Трофимов Б.А. ЖОрХ. 2019, 55, 1938-1941.
  84. Volkov P.A., Telezhkin A.A., Ivanova N.I., Khrapova K.O., Albanov A.I., Gusarova N.K., Trofimov B.A. Russ. J. Org. Chem. 2019, 55, 1971-1974. doi: 10.1134/S1070428019120285
  85. Trofimov B.A., Volkov P.A., Telezhkin A.A., Khrapova K.O., Ivanova N.I., Albanov A.I., Gusarova N.K. J. Org. Chem. 2020, 85, 4927-4936. doi: 10.1021/acs.joc.0c00084
  86. Волков П.А., Гусарова Н.К., Тележкин А.А., Храпова К.О., Иванова Н.И., Албанов А.И., Вакульская Т.И., Хуцишвили С.С., Трофимов Б.А. Изв. АН. Сер. хим. 2020, 1102-1105.
  87. Volkov P.A., Gusarova N.K., Telezhkin A.A., Khrapova K.O., Ivanova N.I., Albanov A.I., Vakul'skaya T.I., Khutsishvili S.S., Trofimov B.A. Russ. Chem. Bull. 2020, 69, 1102-1105. doi: 10.1007/s11172-020-2874-8
  88. Volkov P.A., Khrapova K.O., Telezhkin A.A., Ivanova N.I., Albanov A.I., Gusarova N.K., Trofimov B.A. Org. Lett. 2018, 20, 7388-7391. doi: 10.1021/acs.orglett.8b03061
  89. Волков П.А., Тележкин А.А., Иванова Н.И., Храпова К.О., Гусарова Н.К., Трофимов Б.А. ЖОХ. 2019, 89, 475-478.
  90. Volkov P.A., Telezhkin A.A., Ivanova N.I., Khrapova K.O., Gusarova N.K., Trofimov B.A. Russ. J. Gen. Chem. 2019, 89, 543-545. doi: 10.1134/S1070363219030290
  91. Shchepochkin A.V., Chupakhin O.N., Demina N.S., Averkov M.A., Shimanovskaya T.Yu., Slepukhin P.A., Volkov P.A., Telezhkin A.A., Trofimov B.A., Charushin V.N. Synthesis. 2021, 53, 3791-3798. doi: 10.1055/a-1521-3166
  92. Acheson R.M., Burstall M.L. J. Chem. Soc. 1954, 1954, 3240-3245. doi: 10.1039/JR9540003240
  93. Acheson R.M., Woollard J. J. Chem. Soc., Perkin Trans. 1. 1975, 1975, 438-446. doi: 10.1039/P19750000438
  94. Волков П.А., Храпова К.О., Тележкин А.А., Албанов А.И., Трофимов Б.А. Изв. АН. Сер. хим. 2023, 72, 955-959.
  95. Volkov P.A., Khrapova K.O., Telezhkin A.A., Albanov A.I., Trofimov B.A. Russ. Chem. Bull. 2023, 72, 955-959. doi: 10.1007/s11172-023-3859-5

Copyright (c) 2023 Russian Academy of Sciences

This website uses cookies

You consent to our cookies if you continue to use our website.

About Cookies