Замещенные пирролы на основе кетонов: перспективы использования и достижения в синтезе

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В настоящем обзоре рассмотрено применение пирролов и соединений на их основе в фармацевтике и различных отраслях технологий, в которых пиррол играет ключевую роль, при этом акцент сделан на работы, не вошедшие в ранее опубликованные обзоры. Во второй части обзора обобщены результаты за последние 15 лет в синтезе пирролов из широко распространенных карбонильных соединений, выбор которых обусловлен широкой доступностью данного ряда и возможностью варьировать заместители. Подобная систематизация предлагается впервые. Библиография — 199 ссылок.

Об авторах

Андрей Викторович Иванов

Иркутский институт химии им. А. Е. Фаворского СО РАН

ORCID iD: 0000-0002-6885-6281

Виктория Сергеевна Щербакова

Иркутский институт химии им. А. Е. Фаворского СО РАН

ORCID iD: 0000-0003-2346-6682

Любовь Николаевна Собенина

Иркутский институт химии им. А. Е. Фаворского СО РАН

ORCID iD: 0000-0003-2087-5931

Список литературы

  1. E.Baltazzi, L.I.Krimen. Chem. Rev., 63, 511 (1963)
  2. A.Gossauer. Die Chemie der Pyrrole. (Berlin-Heidelberg; New York: Springer-Verlag, 1974). 433 p.
  3. R.A.Jones, G.P.Bean. The Chemistry of Pyrroles. (London, New York: Academic Press, 1977). 525 p.
  4. A.I.Mikhaleva, N.K.Gusarova. Atsetilen: Reaktsii i Proizvodnye. (Acetylene: Reactions and Derivatives). (Irkutsk: Izd. Ottisk, 2006). 297 p.
  5. B.A.Trofimov, A.I.Mikhaleva, E.Yu.Shmidt, L.N.Sobenina. Khimiya Pirrola. Novye Stranitsy. (Chemistry of Pyrrole. New Pages). (Novosibirsk: Nauka, 2012). 383 p.
  6. D.J.Shrinivas, A.M.Uttam, H.K.Venkatrao, M.A.Tejraj. Curr. Org. Chem., 17, 2279 (2013)
  7. V.Estevez, M.Villacampa, J.C.Menendez. Chem. Soc. Rev., 43, 4633 (2014)
  8. S.Mohamed, S.Mosaad, S.Fathallah. Arch. Pharm., 11, 477 (2014)
  9. M.Pineiro. In Targets in Heterocyclic Systems. Chemistry and Properties. (Eds O.A.Attanasi, P.Merino, D.Spinelli). (Roma: Societa Chimica Italiana, 2017). Vol. 21. Р. 179
  10. S.S.Gholap. Eur. J. Med. Chem., 3, 13 (2016)
  11. D.Tzankova, S.Vladimirova, L.Peikova, M.Georgieva. J. Chem. Technol. Metall., 53, 451 (2018)
  12. I.Azad, F.Hassan, M.Saquib, N.Ahmad, A.R.Khan, A.G.Al-Sehemi, M.Nasibullah. Orient. J. Chem., 34, 1670 (2018)
  13. S.Ahmad, O.Alam, M.Naim, M.Shaquiquzzaman, M.M.Alam, M.Iqbal. Eur. J. Med. Chem., 5, 527 (2018)
  14. S.D.Joshi, U.A.More, V.H.Kulkarni, T.M.Aminabhavi. Curr. Org. Chem., 17, 2279 (2013)
  15. A.Balakrishna, A.Aguiar, P.J.M.Sobral, M.Y.Wani, J.A.Silva, A.J.F.N.Sobral. Sci. Eng., 61, 84 (2019)
  16. G.L.Petri, V.Spano, R.Spatola, R.Holl, M.V.Raimondi, P.Barraja, A.Montalbano. Eur. J. Med. Chem., 208, 112783 (2020)
  17. M.C.A.D.Bianco, D.I.L.F.Marinho, L.V.B.Hoelz, M.M.Bastos, N.Boechat. Pharmaceuticals, 14, 893 (2021)
  18. P.N.Rakendu, T.Aneeja, G.Anilkumar. Asian J. Org. Chem., 10, 2318 (2021)
  19. N.J.Basha, S.M.Basavarajaiah, K.Shyamsunder. Mol. Divers., 25, 1 (2022)
  20. R.H.Mir, P.A.Mir, R.Mohi-Ud-Din, S.Sabreen, M.Maqbool, A.J.Shah, K.Shenmar, S.N.Raza, F.H.Pottoo. Anticancer Agents Med. Chem., 22, 3291 (2022)
  21. E.S.Moghadam, K.Mireskandari, R.Abdel-Jalil, M.Amini. Mini Rev. Med. Chem., 22, 2486 (2022)
  22. T.Shi, G.Yin, X.Wang, Y.Xiong, Y.Peng, S.Li, Y.Zeng, Z.Wang. Green Synth. Cat., 4, 20 (2023)
  23. V.Estevez, M.Villacampa, J.C.Menendez. Chem. Soc. Rev., 39, 4402 (2010)
  24. N.Ghati, A.Roy, S.Bhatnagar, S.Bhati, S.Bhushan, M.Mahendran, A.Thakur, P.Tiwari, T.Dwivedi, K.Mani, R.Gupta, A.Mohan, R.Garg, A.Saxena, R.Guleria, S.Deepti. Trials, 21, 902 (2020)
  25. A.Mueller-Schoell, S.L.Groenland, O.Scherf-Clavel, M.van Dyk, W.Huisinga, R.Michelet, U.Jaehde, N.Steeghs, A.D.R.Huitema, C.Kloft. Eur. J. Clin. Pharmacol., 77, 441 (2021)
  26. N.Cardoe, C.E.Steele. Curr. Med. Res. Opin., 4, 688 (1977)
  27. J.R.Lewis. JAMA, 246, 377 (1981)
  28. H.Bonacorso, H.T.Magalhães, G.M.Dal Forno, F.M.Libero, M.Hoerner, C.P.Frizzo, M.A.P.Martins, N.Zanatta. J. Braz. Chem. Soc., 30, 1189 (2019)
  29. J.da Silva, A.Gingras. Am. J. Emerg. Med., 45, 541 (2021)
  30. M.-A.Burch, A.Keshishian, C.Wittmann, D.Nehrbass, U.Styger, G.Muthukrishnan, D.Arens, V.A.Stadelmann, R.G.Richards, T.F.Moriarty, K.Thompson. Eur. Cell. Mater., 41, 739 (2021)
  31. G.M.Pacifici. Paediatr. Drugs, 15, 363 (2013)
  32. G.Bollag, P.Hirth, J.Tsai, J.Zhang, P.N.Ibrahim, H.Cho, W.Spevak, C.Zhang, Y.Zhang, G.Habets, E.A.Burton, B.Wong, G.Tsang, B.L.West, B.Powell, R.Shellooe, A.Marimuthu, H.Nguyen, K.Y.Zhang, D.R.Artis, J.Schlessinger, F.Su, B.Higgins, R.Iyer, K.D’Andrea, A.Koehler, M.Stumm, P.S.Lin, R.J.Lee, J.Grippo, I.Puzanov, K.B.Kim, A.Ribas, G.A.McArthur, J.A.Sosman, P.B.Chapman, K.T.Flaherty, X.Xu, K.L.Nathanson, K.Nolop. Nature (London), 467, 596 (2010)
  33. A.Tefferi. N. Engl. J. Med., 366, 9 (2012)
  34. K.Samson. Oncology Times, 36, 39 (2014)
  35. H.Kenmotsu, N.Yamamoto, T.Yamanaka, K.Yoshiya, T.Takahashi. J. Clin. Oncol., 38, 2187 (2020)
  36. A.Rossi, S.Ricciardi, P.Maione, F.de Marinis, C.Gridelli. Lung Cancer., 66, 141 (2009)
  37. D.Deidda, G.Lampis, R.Fioravanti, M.Biava, G.C.Porretta, S.Zanetti, R.Pompei. Antimicrob. Agents Chemother., 42, 3035 (1998)
  38. M.Biava, G.C.Porretta, G.Poce, S.Supino, D.Deidda, R.Pompei, P.Molicotti, F.Manetti, M.Botta. J. Med. Chem., 49, 4946 (2006)
  39. S.S.Gholap. Eur. J. Med. Chem., 110, 13 (2016)
  40. M.Biava, G.C.Porretta, G.Poce, A.de Logu, M.Saddi, R.Meleddu, F.Manetti, E.de Rossi, M.Botta. J. Med. Chem., 51, 3644 (2008)
  41. Patent WO 2006/092822A2 (2006)
  42. M.Biava, G.C.Porretta, G.Poce, A.de Logu, R.Meleddu, E.de Rossi, F.Manetti, M.Botta. Eur. J. Med. Chem., 44, 4734 (2009)
  43. S.D.Joshi, U.A.More, S.Sorathiya, D.Koli, T.M.Aminabhavi. Res. Rep. Med. Chem., 5, 1 (2015)
  44. S.D.Joshi, H.M.Vagdevi, V.P.Vaidya, G.S.Gadaginamath. Eur. J. Med. Chem., 43, 1989 (2008)
  45. S.D.Joshi, A.Joshi, H.M.Vagdevi, V.P.Vaidya, G.S.Gadaginamath. Indian J. Pharm. Educ. Res., 44, 148 (2010)
  46. S.D.Joshi, A.Joshi, H.M.Vagdevi, V.P.Vaidya, G.S.Gadaginamath. Indian J. Heterocycl. Chem., 19, 221 (2010)
  47. S.D.Joshi, Y.More, H.M.Vagdevi, V.P.Vaidya, G.S.Gadaginamath, V.H.Kulkarni. Med. Chem. Res., 22, 1073 (2013)
  48. S.D.Joshi, K.Manish, A.Badiger. Med. Chem. Res., 22, 869 (2013)
  49. L.N.Rogoza, N.F.Salakhutdinov, G.A.Tolstikov. Chem. Sus. Devel., 18, 343 (2010)
  50. D.Schillaci, S.Petruso, V.Sciortino. Int. J. Antimicrob. Agents., 25, 338 (2005)
  51. M.V.Raimondi, S.C.D.Schillaci, S.Petruso. Eur. J. Med. Chem., 41, 1439 (2006)
  52. S.Cascioferro, M.V.Raimondi, M.G.Cusimano, D.Raffa, B.Maggio, G.Daidone, D.Schillaci. Molecules, 20, 21658 (2015)
  53. K.M.H.Hilmy, M.M.A.Khalifa, M.A.A.Hawata, R.M.A.Keshk, A.A.El-Torgman. Eur. J. Med. Chem., 45, 5243 (2010)
  54. M.S.A.El-Gaby, A.M.Gaber, A.A.Atalla, K.A.Abd.Al-Wahab. Il Farmaco, 57, 613 (2002)
  55. G.H.Jana, S.Jain, S.K.Arora, N.Sinha. Bioorg. Med. Chem. Lett., 15, 3592 (2005)
  56. L.Dyson, A.D.Wright, K.A.Young, J.A.Sakoff, A.McCluskey. Bioorg. Med. Chem., 22, 1690 (2014)
  57. M.V.Raimondi, A.Presentato, G.L.Petri, M.Buttacavoli, A.Ribaudo. Antibiotics, 9, 292 (2020)
  58. M.G.Brasca, P.Gnocchi, M.Nesi, N.Amboldi, N.Avanzi, J.Bertrand, S.Bindi, G.Canevari, D.Casero, M.Ciomei, N.Colombo, S.Cribioli, G.Fachin, E.R.Felder, A.Galvani, A.Isacchi, I.Motto, A.Panzeri, D.Donati. Bioorg. Med. Chem., 23, 2387 (2015)
  59. N.K.Rasal, R.B.Sonawane, S.V.Jagtap. Bioorg. Chem., 97, 103660 (2020)
  60. L.Zhang, Q.Zheng, Y.Yang, H.Zhou, X.Gong, S.Zhao, C.Fan. Eur. J. Med. Chem., 82, 139 (2014)
  61. G.La.Regina, R.Bai, A.Coluccia, V.Famiglini, S.Pelliccia, S.Passacantilli, C.Mazzoccoli, V.Ruggieri, L.Sisinni, A.Bolognesi, W.M.Rensen, A.Miele, M.Nalli, R.Alfonsi, L.D.Marcotullio, A.Gulino, A.Brancale, E.Novellino, G.Dondio, S.Vultaggio, M.Varasi, C.Mercurio, E.Hamel, P.Lavia, R.Silvestri. J. Med. Chem., 57, 6531 (2014)
  62. R.La Giuseppe, R.Bai, A.Coluccia, V.Famiglini, S.Passacantilli, V.Naccarato, G.Ortar, C.Mazzoccoli, V.Ruggieri, F.Agriesti, C.Piccoli, T.Tataranni, M.Nalli, A.Brancale, S.Vultaggio, C.Mercurio, M.Varasi, C.Saponaro, S.Sergio, M.Maffia, A.M.L.Coluccia, E.Hamel, R.Silvestri. ACS Med. Chem. Lett., 8, 521 (2017)
  63. S.A.F.Rostom, A.A.Bekhit. Eur. J. Med. Chem., 92, 712 (2015)
  64. Y.Liu, C.Zhang, H.Zhang, M.Li, J.Yuan, Y.Zhang, J.Zhou, H.Guo, Y.Du, L.Wang, L.Ren. Eur. J. Med. Chem., 93, 142 (2015)
  65. H.Kuznietsova, N.Dziubenko, I.Byelinska, V.Hurmach, A.Bychko, O.Lynchak, D.Milokhov, O.Khilya, V.Rybalchenko. J. Drug Targeting, 28, 547 (2020)
  66. M.I.L.Soares, A.F.Brito, M.Laranjo, J.A.Paixao, M.F.Botelho, T.M.V.D.Pinhoe Melo. Eur. J. Med. Chem., 60, 254 (2013)
  67. B.Parrino, A.Carbone, C.Ciancimino, V.Spano, A.Montalbano, P.Barraja, G.Cirrincione, P.Diana, C.Sissi, M.Palumbo, O.Pinato, M.Pennati, G.Beretta, M.Folini, P.Matyus, B.Balogh, N.Zaffaroni. Eur. J. Med. Chem., 94, 149 (2015)
  68. G.Li Petri, V.Spanò, R.Spatola, R.Holl, M.V.Raimondi, P.Barraja, A.Montalbano. Eur. J. Med. Chem., 208, 112783 (2020)
  69. E.Mateev, M.Georgieva, A.Zlatkov. J. Pharm. Pharm. Sci., 25, 24 (2022)
  70. A.Wiegard, W.Hanekamp, K.Griessbach, J.Fabian, M.Lehr. Eur. J. Med. Chem., 48, 153 (2012)
  71. Y.Harrak, G.Rosell, G.Daidone, S.Plescia, D.Schillaci, M.D.Pujol. Bioorg. Med. Chem., 15, 4876 (2007)
  72. M.da C.A.D.Bianco, D.I.L.F.Marinho, L.V.B.Hoelz, M.M.Bastos, N.Boechat. Pharmaceuticals, 14, 893 (2021)
  73. X.-Y.He, Lu.Lu, J.Qiu, Z.Peng, Yu.Fei, J.Xing-Kai, L.Lin, J.Shibo, L.Shuwen, X.Lan. Bioorg. Med. Chem., 21, 7539 (2013)
  74. J.Qiu, T.Liang, J.Wu, F.Yu, X.He, Y.Tian, L.Xie, S.Jiang, H.Liu, L.Li. Front. Pharmacol., 10, 859 (2019)
  75. A.Ianevski, R.Yao, M.H.Fenstad, S.Biza, E.Zusinaite, T.Reisberg, H.Lysvand, K.Løseth, V.M.Landsem, J.F.Malmring, V.Oksenych, S.S.Erlandsen, P.A.Aas, L.Hagen, C.H.Pettersen, T.Tenson, J.E.Afset, S.A.Nordbø, M.Bjørås, D.E.Kainov. Viruses, 12, 642 (2020)
  76. P.Rao, A.Shukla, P.Parmar, R.M.Rawal, B.Patel, M.Saraf, D.Goswami. Biophys. Chem., 264, 106425 (2020)
  77. S.Lu, X.Pan, D.Chen, X.Xie, Y.Wu. Bioorg. Chem., 107, 104619 (2021)
  78. Z.Fakhar, S.Khan, S.Y.Alomar, A.Alkhuriji, A.Ahmad. Sci. Rep., 11, 234 (2021)
  79. F.S.Varghese, E.van Woudenbergh, G.J.Overheul, M.J.Eleveld, L.Kurver, N.van Heerbeek, A.van Laarhoven, P.Miesen, G.den Hartog, M.I.de Jonge, R.P.van Rij. Viruses, 13, 282 (2021)
  80. G.Campiani, S.Butini, C.Fattorusso, B.Catalanotti, S.Gemma, V.Nacci, E.Morelli, A.Cagnotto, I.Mereghetti, T.Mennini, M.Carli, P.Minetti, M.Assunta Di Cesare, D.Mastroianni, N.Scafetta, B.Galletti, M.Antonietta Stasi, M.Castorina, L.Pacifici, M.Vertechy, S.D.Serio, O.Ghirardi, O.Tinti, P.Carminati. J. Med. Chem., 47, 143 (2004)
  81. F.Scala, E.Fattorusso, M.Menna, O.Taglialatela-Scafati, M.Tierney, M.Kaiser, D.Tasdemir. Mar. Drugs, 8, 2162 (2010)
  82. D.T.Mahajan, V.H.Masand, K.N.Patil, T.B.Hadda, V.Rastija. Med. Chem. Res., 22, 2284 (2013)
  83. R.D.Charan, G.Schlingmann, V.S.Bernan, X.Feng, G.T.Carter. J. Nat. Prod., 69, 29 (2006)
  84. A.A.Abdelhamid, K.S.M.Salama, A.M.Elsayed, M.A.Gad, M.Aleem El Abd, A.A.El-Remaily. ACS Omega, 7, 3990 (2022)
  85. T.Biftu, D.Feng, M.Ponpipom, N.Girotra, G.-B.Liang, X.Qain, R.Bugianesi, J.Simeone, L.Chang, A.Gurnett, P.Liberator, P.Dulski, P.S.Leavitt, T.Grumley, A.Misura, T.Murphy, S.Rattray, S.Samaras, T.Tamas, J.Mathew, C.Brown, D.Thompson, D.Schmatz, M.Fisher, M.Wyvratt. Bioorg. Med. Chem. Lett., 15, 3296 (2005)
  86. A.Diaz, J.M.Vasquez Vallejo, A.Martinez Duran. J. Res. Develop., 25, 42 (1981)
  87. M.Harjo, M.Järvekülg, T.Tamm, T.F.Otero, R.Kiefer. PLoS ONE, 15, e0232851 (2020)
  88. A.Islam, Z.-y.Liu, R.-x.Peng, W.-g.Jiang, T.Lei, W.Li, L.Zhang, R.-j.Yang, Q.Guan, Z.-y.Ge. Chin. J. Polym. Sci., 35, 171 (2017)
  89. Y.-S.Jung, K.Hwang, Y.-J.Heo, J.-E.Kim, D.Lee, C.-H.Lee, H.-I.Joh, J.-S.Yeo, D.-Y.Kim. ACS Appl. Mater. Interfaces, 9, 27832 (2017)
  90. F.Lin, W.Huang, H.Sun, J.Xin, H.Zeng, T.Yang, M.Li, X.Zhang, W.Ma, Y.Liang. Chem. Mat., 29, 5636 (2017)
  91. Z.Wang, M.Liang, H.Dong, P.Gao, Y.Su, P.Cai, S.Ding, J.Chen, S.Xue. Org. Lett., 19, 3711 (2017)
  92. X.Liu, J.Wu, Q.Guo, Y.Yang, H.Luo, Q.Liu, X.Wang, X.He, M.Huang, Z.Lan. J. Mater. Chem., 7, 11764 (2019)
  93. J.Ji, W.Zhu, J.Li, P.Wang, Y.Liang, W.Zhang, X.Yin, B.Wu, G.Li. ACS Appl. Mater. Interfaces, 9, 19124 (2017)
  94. P.Gómez, M.Más-Montoya, I.da Silva, J.P.Cerón-Carrasco, A.Tárraga, D.Curiel. Cryst. Growth Des., 17, 3371 (2017)
  95. H.Zhang, Z.Iqbal, Z-E.Chen, Yan-P.Hong. RSC Adv., 7, 35598 (2017)
  96. J.Zhou, X.Yin, Z.Dong, A.Ali, Z.Song, N.Shrestha, S.S.Bista, Q.Bao, R.J.Ellingson, Y.Yan, W.Tang. Angew. Chem., Int. Ed., 58, 13717 (2019)
  97. S.Mabrouk, M.Zhang, Z.Wang, M.Liang, B.Bahrami, Y.Wu, J.Wu, Q.Qiao, S.Yang. J. Mater. Chem. A, 6, 7950 (2018)
  98. R.Domínguez, N.F.Montcada, P.de la Cruz, E.Palomares, F.Langa. ChemPlusChem, 82, 1096 (2017)
  99. M.Krzeszewski, D.Gryko, D.T.Gryko. Acc. Chem. Res., 50, 2334 (2017)
  100. S.Sugiura, H.Maeda. Org. Biomol. Chem., 18, 4433 (2020)
  101. B.A.Paulraj, P.Murugesan, A.V.Swaminathan, J.Madhavan, V.S.Rajadurai, P.M.Johnson. Comput. Mater. Sci., 162, 359 (2019)
  102. J.Chen, A.Burghart, A.Derecskei-Kovacs, K.Burgess. J. Org. Chem., 65, 2900 (2000)
  103. M.Albrecht, A.Lippach, M.P.Exner, J.Jerbi, M.Springborg, N.Budisa, G.Wenz. Org. Biomol. Chem., 13, 6728 (2015)
  104. N.Boens, L.Wang, V.Leen, P.Yuan, B.Verbelen, W.Dehaen, M.Van der Auweraer, W.D.De Borggraeve, L.Van Meervelt, J.Jacobs, D.Beljonne, C.Tonnelé, R.Lazzaroni, M.J.Ruedas-Rama, A.Orte, L.Crovetto, E.M.Talavera, J.M.Alvarez-Pez. J. Phys. Chem. A, 118, 1576 (2014)
  105. M.Poddar, R.Misra. Coord. Chem. Rev., 421, 213462 (2020)
  106. H.Lu, Z.Shen. Front. Chem., 8, 290 (2020)
  107. B.Matarranz, G.Fernández. Chem. Phys. Rev., 2, 041304 (2021)
  108. L.Yuan, W.Lin, K.Zheng, L.He, W.Huang. Chem. Soc. Rev., 42, 622 (2013)
  109. B.Bertrand, K.Passador, C.Goze, F.Denat, E.Bodio, M.Salmain. Coord. Chem. Rev., 358, 108 (2018)
  110. A.Turksoy, D.Yildiz, E.U.Akkaya. Coord. Chem. Rev., 379, 47 (2019)
  111. T.Zhang, C.Ma, T.Sun, Z.Xie. Coord. Chem. Rev., 390, 76 (2019)
  112. V.Lakshmi, R.Sharma, M.Ravikanth. Rep. Org. Chem., 6, 1 (2016)
  113. T.Kowad, H.Maeda, K.Kikuchi. Chem. Soc. Rev., 44, 4953 (2015)
  114. C.S.Kue, S.Y.Ng, S.H.Voon, A.Kamkaew, L.Y.Chung, L.V.Kiew, H.B.Lee. Photochem. Photobiol. Sci., 17, 1691 (2018)
  115. L.N.Sobenina, O.V.Petrova, K.B.Petrushenko, I.A.Ushakov, A.I.Mikhaleva, R.Meallet-Renault, B.A.Trofimov. Eur. J. Org. Chem., 2013 (19), 4107 (2013)
  116. K.B.Petrushenko, I.K.Petrushenko, O.V.Petrova, L.N.Sobenina, I.A.Ushakov, B.A.Trofimov. Asian J. Org. Chem., 6, 852 (2017)
  117. A.V.Gadomska, A.V.Nevidimov, S.A.Tovstun, O.V.Petrova, L.N.Sobenina, B.A.Trofimov, V.F.Razumov. Spectrochim. Acta, Part A, 254, 119632 (2021)
  118. A.V.Gadomska, A.V.Nevidimov, S.A.Tovstun, O.V.Petrova, L.N.Sobenina, B.A.Trofimov, V.F.Razumov. High Energy Chem., 55, 179 (2021)
  119. Patent RU 2717308C1 (2019)
  120. I.S.Trukhan, D.N.Tomilin, N.N.Dremina, L.N.Sobenina, M.G.Shurygin, K.B.Petrushenko, I.K.Petrushenko, B.A.Trofimov, I.A.Shurygina. Molecules, 27, 5018 (2022)
  121. H.Wang, W.Zhao, X.Liu, S.Wang, Y.Wang. ACS Appl. Bio Mater., 3, 593 (2020)
  122. G.Li, X.Zhang, W.Zhao, W.Zhao, F.Li, K.Xiao, Q.I.Yu, S.Liu, Q.Zhao. ACS Appl. Mater. Interfaces, 12, 20180 (2020)
  123. G.Gupta, A.Das, K.C.Park, A.Tron, H.Kim, J.Mun, N.Mandal, K.-W.Chi, C.Y.Lee. Inorg. Chem., 56, 4615 (2017)
  124. G.Gupta, A.Das, S.W.Lee, J.Y.Ryu, J.Lee, N.Nagesh, N.Mandal, C.Y.Lee. J. Organomet. Chem., 868, 86 (2018)
  125. G.Gupta, Y.Sun, A.Das, P.J.Stang, C.Y.Lee. Coord. Chem. Rev., 452, 214308 (2022)
  126. S.Kusaka, R.Sakamoto, Y.Kitagawa, M.Okumura, H.Nishihara. Chem. – Asian J., 7, 907 (2012)
  127. S.Erten-Ela, O.Vakuliuk, A.Tarnowska, K.Ocakoglu, D.T.Gryko. Spectrochim. Acta, Part A, 135, 676 (2015)
  128. O.Miguel, P.Zúñiga, Á.G.Sathicq, J.Jobanny, M.Zambrano, G.P.Romanelli. Cur. Org. Synt., 14, 1 (2017)
  129. M.Leonardi, V.Estévez, M.Villacampa, J.C.Menéndez. Synthesis, 51, 816 (2019)
  130. I.V.Efimov, L.N.Kulikova, A.R.Miftyakhova, M.D.Matveeva, L.G.Voskressensky. Chemistry Select., 6, e202103486 (2021)
  131. E.Abele, E.Lucevics. Heterocycles, 53, 2285 (2000)
  132. A.I.Mikhaleva, E.Yu.Schmidt. In Selected Methods for Synthesis and Modification of Heterocycles. (Ed. V.G.Kartsev). (Moscow: IBS Press, 2002). P. 334
  133. R.J.Tedeschi. In Acetylene. Encyclopedia of Physical Science and Technology. (3rd Edn.) (Ed. R.A.Meyers). (San Diego, CA: Academic Press, 2001). P. 55
  134. Z.Rappoport, J.F.Liebman. In The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids (Chichester: Wiley, 2008). P. 241
  135. Z.Wang. In Comprehensive Organic Name Reactions and Reagents. Pt 3. Paragraph 626 (London: Wiley, 2009)
  136. D.N.Tomilin, E.F.Sagitova, K.B.Petrushenko, L.N.Sobenina, I.A.Ushakov, G.Q.Yang, R.Hu, B.A.Trofimov. Dyes Pigm., 176, 108228 (2020)
  137. E.F.Sagitova, D.N.Tomilin, O.V.Petrova, A.B.Budaev, L.N.Sobenina, B.A.Trofimov, G.Q.Yang, R.Hu. Mendeleev Commun., 29, 658 (2019)
  138. A.B.Budaev, A.V.Ivanov, O.V.Petrova, V.A.Samsonov, I.A.Ushakov, A.Ya.Tikhonov, L.N.Sobenina, B.A.Trofimov. Mendeleev. Commun., 29, 53 (2019)
  139. A.B.Budaev, A.V.Ivanov, O.V.Petrova, A.Ya.Tikhonov, V.A.Samsonov, L.N.Sobenina, B.A.Trofimov. Russ. J. Org. Chem. 55, 273 (2019)
  140. O.V.Petrova, L.N.Sobenina, I.A.Ushakov, A.B.Budaev, A.V.Ivanov, V.A.Samsonov, A.Ya.Tikhonov, B.A.Trofimov. Mendeleev Commun., 27, 344 (2017)
  141. E.Yu.Schmidt, A.I.Mikhaleva, A.M.Vasil’tsov, A.B.Zaitsev, N.V.Zorina. ARKIVOC, vii, 11 (2005)
  142. A.I.Mikhaleva, E.Yu.Schmidt, A.V.Ivanov, A.M.Vasil’tsov, E.Yu.Senotrusova, N.I.Protsuk. Russ. J. Org. Chem., 43, 228 (2007)
  143. A.M.Vasil’tsov, A.V.Ivanov, A.I.Mikhaleva, B.A.Trofimov. Tetrahedron Lett., 51, 1690 (2010)
  144. B.A.Trofimov, A.V.Ivanov, E.Yu.Schmidt, A.I.Mikhaleva. Chem. Heterocycl. Compd., 46, 762 (2010)
  145. S.E.Korostova, A.I.Mikhaleva, L.N.Sobenina, S.G.Shevchenko, R.I.Polovnikova. Zh. Org. Khim., 3, 492 (1986)
  146. A.I.Mikhaleva, B.A.Trofimov, A.N.Vasil’ev, G.A.Komarova, V.I.Skorobogatova. Chem. Heterocycl. Compd., 18, 920 (1982)
  147. B.A.Trofimov, A.I.Mikhaleva. Izv. ANauk SSSR. Ser. Khim., 12, 2840 (1979)
  148. B.A.Trofimov, A.I.Mikhaleva, A.V.Ivanov, V.S.Shcherbakova, I.A.Ushakov. Tetrahedron, 71, 124 (2015)
  149. A.V.Ivanov, V.S.Shcherbakova, A.I.Mikhaleva, B.A.Trofimov. Russ. J. Org. Chem., 50, 1775 (2014)
  150. A.V.Ivanov, V.S.Barnakova, A.I.Mikhaleva, B.A.Trofimov. Russ. Chem. Bull., 62, 2557 (2013)
  151. A.Yu.Kritskaya, N.A.Bumagina, E.V.Antina, A.A.Ksenofontov, M.B.Berezin,·A.S.Semeikin. J. Fluoresc., 28, 393 (2018)
  152. K.S.Rodygin, G.Werner, F.A.Kucherov, V.P.Ananikov. Chem. – Asian J., 11, 965 (2016)
  153. R.Fu, Z.Li, L.Gao. Prog. Chem., 31, 1303 (2019)
  154. D.A.Shabalin, A.Yu.Dubovtsev, E.Yu.Schmidt, B.A.Trofimov. Chem. Select., 5, 3434 (2020)
  155. N.Kaewchangwat, R.Sukato, V.Vchirawongkwin, T.Vilaivan, M.Sukwattanasinitt, S.Wacharasindhu. Green Chem., 17, 460 (2015)
  156. L.Ran, Z.-H.Ren, Y.-Y.Wang, Z.-H.Guan. Green Chem., 16, 112 (2014)
  157. Y.Xie, Y.Li, X.Chen, Y.Liua, W.Zhang. Org. Chem. Front., 5, 1698 (2018)
  158. Z.Xu, N.Xian, H.Chen, G.-J.Deng, H.Huang. Chin. J. Chem., 39, 1175 (2021)
  159. X.Tang, L.Huang, C.Qi, W.Wu, H.Jiang. Chem. Commun., 49, 9597 (2013)
  160. H.-B.Yang, N.Selander. Chem. – Eur. J., 23, 1779 (2017)
  161. K.Singh, M.Vellakkaran, D.Banerjee. Green Chem., 20, 2250 (2018)
  162. J.Wang, M.Tang, W.Gu, S.Huang, L.-G.Xie. J. Org Chem., 87, 12482 (2022)
  163. B.A.Shainyan. Russ. Chem. Rev., 91 (9), RCR5052 (2022)
  164. J.Vaitla, A.Bayer, K.H.Hopmann. Angew. Chem., Int. Ed., 56, 1 (2017)
  165. D.Chang, J.Chen, Y.Liu, H.Huang, A.Qin, G.-J.Deng. J. Org. Chem., 86, 110 (2021)
  166. T.T.Dang, A.M.Seayad. Chem. – Asian. J., 12, 2383 (2017)
  167. X.Wu, K.Li, S.Wang, C.Liu, A.Lei. Org. Lett., 18, 56 (2016)
  168. M.Fatahpour, N.Hazeri, M.T.Maghsoodlou, M.Lashkari. J. Iranian Chem. Soc., 16, 111 (2019)
  169. M.T.Huggins, T.Kesharwani, J.Buttrick, C.Nicholson. J. Chem. Educ., 97, 1425 (2020)
  170. M.J.Kim, S. M.Gaube, M.H.R.Beh, C.D.Smith, A.Thompson. RSC Adv., 9, 31773 (2019)
  171. G.Fang, J.Liu, J.Fu, Q.Liu, X.Bi. Org. Lett., 19, 1346 (2017)
  172. X.Jiang, T.Zhang, C.Sun, Y.Meng, L.Xiao. Chin. Chem. Lett., 30, 1055 (2019)
  173. A.F.Khlebnikov, O.A.Tomashenko, L.D.Funt, M.S.Novikov. Org. Biomol. Chem., 12, 6598 (2014)
  174. A.V.Galenko, A.F.Khlebnikov, M.S.Novikov, M.S.Avdontceva. Tetrahedron, 71, 1940 (2015)
  175. W.Wu, S.Wen, X.Zhang, Q.Lin, Z.Weng. Org. Lett., 23, 6352 (2021)
  176. J.Chen, C.Li, Y.Zhou, C.Sun, T.Sun. ChemCatChem., 11, 1943 (2019)
  177. Patent WO 2017002849 (2017)
  178. E.Vessally. RSC Adv., 6, 18619 (2016)
  179. S.Arshadi, E.Vessally, L.Edjlali, E.Ghorbani-Kalhor, R.Hosseinzadeh-Khanmiri. RSC Adv., 7, 13198 (2017)
  180. G.Cheng, W.Lv, L.Xue. Green Chem., 20, 4414 (2018)
  181. B.Ge, W.Lv, J.Yu, S.Xiao, G.Cheng. Org. Chem. Front., 5, 3103 (2018)
  182. N.Kanova, B.A.Dundar, Y.Kelgokmen, M.Zora. J. Org. Chem., 86, 6289 (2021)
  183. Q.Zhen, R.Li, L.Qi, K.Hu, X.Yao, Y.Shao. J. Chen. Org. Chem. Front., 7, 286 (2020)
  184. H.Liu, C.Qi, L.Wang, Y.Guo, D.Li, H. Jiang. J. Org. Chem., 86, 9610 (2021)
  185. B.A.Trofimov, A.I.Michaleva, E.Yu.Shmidt, L.N.Sobenina. Adv. Heterocycl. Chem., 209, 99 (2010)
  186. B.Eftekhari-Sis, M.Zirak, A.Akbari. Chem. Rev., 113, 2958 (2013)
  187. R.Javahershenas, F.M.Arlan, R.H.Prager, J.Khalafy. ARKIVOC, i, 117 (2020)
  188. X.Chang, X.Yang, Z.Chen, W.Zhong. Synlett, 30, 1431 (2019)
  189. F.Nezhad-Shahrokhabadi, M.Anary-Abbasinejad. J. Iran Chem. Soc., 19, 2655 (2022)
  190. M.Anary-Abbasinejada, F.Nezhad-Shahrokhabadi, M.Mohammadi. Mol. Divers., 24, 1205 (2020)
  191. N.N.Kolos, V.V.Zubar, I.V.Omelchenko, V.I.Musatov. Chem. Heterocycl. Compd., 52, 237 (2016)
  192. P.K.Shirsat, N.B.Khomane, P.R.Mali, R.R.Maddi, J.B.Nanubolu, H.M.Meshram. Chem. Select., 2, 11218 (2017)
  193. S.Das. RSC Adv., 18, 18875 (2020)
  194. H.G.Bonacorso, H.T.Magalhães, G.M.Dal Forno, F.M.Libero, M.Hoerner, C.P.Frizzo, M.A.P.Martinsa, N.Zanattaa. J. Braz. Chem. Soc., 30, 1189 (2019)
  195. X.-M.Tan, Q.-M.Lai, Z.-W.Yang, X.Long, H.-L.Zhou, X.-L.You, X.-J.Jiang, H.-L.Cui. Tetrahedron Lett., 58, 163 (2017)
  196. L.Kurti. Appications of Named Reactions in Organic Synthesis. (Ed. B.Czako). (Elsevier, 2005). 864 p.
  197. J.Luo, D.Lu, Y.Peng, Q.Tang. Asian J. Org. Chem., 6, 1546 (2017)
  198. L.Hu, J.Luo, D.Lu, Q.Tang. Tetrahedron Lett., 59, 1698 (2018)
  199. V.Rajeshkumar, C.Neelamegam, S.Anandan. Synthesis, 51, 4023 (2019)

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