Substituted pyrroles based on ketones: prospects of application and advances in synthesis
- Authors: Ivanov A.V.1, Shcherbakova V.S.1, Sobenina L.N.1
-
Affiliations:
- A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
- Issue: Vol 92, No 9 (2023)
- Pages: RCR5090
- Section: Articles
- URL: https://journals.rcsi.science/0042-1308/article/view/252025
- DOI: https://doi.org/10.59761/RCR5090
- ID: 252025
Cite item
Full Text
Abstract
The review addresses the applications of pyrroles and compounds based on them in pharmaceutics and various branches of technology in which pyrrole plays a key role. The emphasis is put on the studies that were not covered in the previous reviews. The second part of the review summarizes the published data of the last 15 years on the synthesis of pyrroles from widely encountered carbonyl compounds, which were chosen because of ready availability and the possibility of varying the substituents. This type of systematization is proposed for the first time.The bibliography includes 199 references.The bibliography includes 199 references
About the authors
Andrey Viktorovich Ivanov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
ORCID iD: 0000-0002-6885-6281
Victoria Sergeevna Shcherbakova
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
ORCID iD: 0000-0003-2346-6682
Lyubov Nikolaevna Sobenina
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
ORCID iD: 0000-0003-2087-5931
References
- E.Baltazzi, L.I.Krimen. Chem. Rev., 63, 511 (1963)
- A.Gossauer. Die Chemie der Pyrrole. (Berlin-Heidelberg; New York: Springer-Verlag, 1974). 433 p.
- R.A.Jones, G.P.Bean. The Chemistry of Pyrroles. (London, New York: Academic Press, 1977). 525 p.
- A.I.Mikhaleva, N.K.Gusarova. Atsetilen: Reaktsii i Proizvodnye. (Acetylene: Reactions and Derivatives). (Irkutsk: Izd. Ottisk, 2006). 297 p.
- 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.
- D.J.Shrinivas, A.M.Uttam, H.K.Venkatrao, M.A.Tejraj. Curr. Org. Chem., 17, 2279 (2013)
- V.Estevez, M.Villacampa, J.C.Menendez. Chem. Soc. Rev., 43, 4633 (2014)
- S.Mohamed, S.Mosaad, S.Fathallah. Arch. Pharm., 11, 477 (2014)
- 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
- S.S.Gholap. Eur. J. Med. Chem., 3, 13 (2016)
- D.Tzankova, S.Vladimirova, L.Peikova, M.Georgieva. J. Chem. Technol. Metall., 53, 451 (2018)
- I.Azad, F.Hassan, M.Saquib, N.Ahmad, A.R.Khan, A.G.Al-Sehemi, M.Nasibullah. Orient. J. Chem., 34, 1670 (2018)
- S.Ahmad, O.Alam, M.Naim, M.Shaquiquzzaman, M.M.Alam, M.Iqbal. Eur. J. Med. Chem., 5, 527 (2018)
- S.D.Joshi, U.A.More, V.H.Kulkarni, T.M.Aminabhavi. Curr. Org. Chem., 17, 2279 (2013)
- A.Balakrishna, A.Aguiar, P.J.M.Sobral, M.Y.Wani, J.A.Silva, A.J.F.N.Sobral. Sci. Eng., 61, 84 (2019)
- G.L.Petri, V.Spano, R.Spatola, R.Holl, M.V.Raimondi, P.Barraja, A.Montalbano. Eur. J. Med. Chem., 208, 112783 (2020)
- M.C.A.D.Bianco, D.I.L.F.Marinho, L.V.B.Hoelz, M.M.Bastos, N.Boechat. Pharmaceuticals, 14, 893 (2021)
- P.N.Rakendu, T.Aneeja, G.Anilkumar. Asian J. Org. Chem., 10, 2318 (2021)
- N.J.Basha, S.M.Basavarajaiah, K.Shyamsunder. Mol. Divers., 25, 1 (2022)
- 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)
- E.S.Moghadam, K.Mireskandari, R.Abdel-Jalil, M.Amini. Mini Rev. Med. Chem., 22, 2486 (2022)
- T.Shi, G.Yin, X.Wang, Y.Xiong, Y.Peng, S.Li, Y.Zeng, Z.Wang. Green Synth. Cat., 4, 20 (2023)
- V.Estevez, M.Villacampa, J.C.Menendez. Chem. Soc. Rev., 39, 4402 (2010)
- 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)
- 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)
- N.Cardoe, C.E.Steele. Curr. Med. Res. Opin., 4, 688 (1977)
- J.R.Lewis. JAMA, 246, 377 (1981)
- 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)
- J.da Silva, A.Gingras. Am. J. Emerg. Med., 45, 541 (2021)
- 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)
- G.M.Pacifici. Paediatr. Drugs, 15, 363 (2013)
- 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)
- A.Tefferi. N. Engl. J. Med., 366, 9 (2012)
- K.Samson. Oncology Times, 36, 39 (2014)
- H.Kenmotsu, N.Yamamoto, T.Yamanaka, K.Yoshiya, T.Takahashi. J. Clin. Oncol., 38, 2187 (2020)
- A.Rossi, S.Ricciardi, P.Maione, F.de Marinis, C.Gridelli. Lung Cancer., 66, 141 (2009)
- D.Deidda, G.Lampis, R.Fioravanti, M.Biava, G.C.Porretta, S.Zanetti, R.Pompei. Antimicrob. Agents Chemother., 42, 3035 (1998)
- 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)
- S.S.Gholap. Eur. J. Med. Chem., 110, 13 (2016)
- 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)
- Patent WO 2006/092822A2 (2006)
- 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)
- S.D.Joshi, U.A.More, S.Sorathiya, D.Koli, T.M.Aminabhavi. Res. Rep. Med. Chem., 5, 1 (2015)
- S.D.Joshi, H.M.Vagdevi, V.P.Vaidya, G.S.Gadaginamath. Eur. J. Med. Chem., 43, 1989 (2008)
- S.D.Joshi, A.Joshi, H.M.Vagdevi, V.P.Vaidya, G.S.Gadaginamath. Indian J. Pharm. Educ. Res., 44, 148 (2010)
- S.D.Joshi, A.Joshi, H.M.Vagdevi, V.P.Vaidya, G.S.Gadaginamath. Indian J. Heterocycl. Chem., 19, 221 (2010)
- S.D.Joshi, Y.More, H.M.Vagdevi, V.P.Vaidya, G.S.Gadaginamath, V.H.Kulkarni. Med. Chem. Res., 22, 1073 (2013)
- S.D.Joshi, K.Manish, A.Badiger. Med. Chem. Res., 22, 869 (2013)
- L.N.Rogoza, N.F.Salakhutdinov, G.A.Tolstikov. Chem. Sus. Devel., 18, 343 (2010)
- D.Schillaci, S.Petruso, V.Sciortino. Int. J. Antimicrob. Agents., 25, 338 (2005)
- M.V.Raimondi, S.C.D.Schillaci, S.Petruso. Eur. J. Med. Chem., 41, 1439 (2006)
- S.Cascioferro, M.V.Raimondi, M.G.Cusimano, D.Raffa, B.Maggio, G.Daidone, D.Schillaci. Molecules, 20, 21658 (2015)
- 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)
- M.S.A.El-Gaby, A.M.Gaber, A.A.Atalla, K.A.Abd.Al-Wahab. Il Farmaco, 57, 613 (2002)
- G.H.Jana, S.Jain, S.K.Arora, N.Sinha. Bioorg. Med. Chem. Lett., 15, 3592 (2005)
- L.Dyson, A.D.Wright, K.A.Young, J.A.Sakoff, A.McCluskey. Bioorg. Med. Chem., 22, 1690 (2014)
- M.V.Raimondi, A.Presentato, G.L.Petri, M.Buttacavoli, A.Ribaudo. Antibiotics, 9, 292 (2020)
- 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)
- N.K.Rasal, R.B.Sonawane, S.V.Jagtap. Bioorg. Chem., 97, 103660 (2020)
- L.Zhang, Q.Zheng, Y.Yang, H.Zhou, X.Gong, S.Zhao, C.Fan. Eur. J. Med. Chem., 82, 139 (2014)
- 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)
- 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)
- S.A.F.Rostom, A.A.Bekhit. Eur. J. Med. Chem., 92, 712 (2015)
- 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)
- H.Kuznietsova, N.Dziubenko, I.Byelinska, V.Hurmach, A.Bychko, O.Lynchak, D.Milokhov, O.Khilya, V.Rybalchenko. J. Drug Targeting, 28, 547 (2020)
- 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)
- 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)
- G.Li Petri, V.Spanò, R.Spatola, R.Holl, M.V.Raimondi, P.Barraja, A.Montalbano. Eur. J. Med. Chem., 208, 112783 (2020)
- E.Mateev, M.Georgieva, A.Zlatkov. J. Pharm. Pharm. Sci., 25, 24 (2022)
- A.Wiegard, W.Hanekamp, K.Griessbach, J.Fabian, M.Lehr. Eur. J. Med. Chem., 48, 153 (2012)
- Y.Harrak, G.Rosell, G.Daidone, S.Plescia, D.Schillaci, M.D.Pujol. Bioorg. Med. Chem., 15, 4876 (2007)
- M.da C.A.D.Bianco, D.I.L.F.Marinho, L.V.B.Hoelz, M.M.Bastos, N.Boechat. Pharmaceuticals, 14, 893 (2021)
- 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)
- 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)
- 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)
- P.Rao, A.Shukla, P.Parmar, R.M.Rawal, B.Patel, M.Saraf, D.Goswami. Biophys. Chem., 264, 106425 (2020)
- S.Lu, X.Pan, D.Chen, X.Xie, Y.Wu. Bioorg. Chem., 107, 104619 (2021)
- Z.Fakhar, S.Khan, S.Y.Alomar, A.Alkhuriji, A.Ahmad. Sci. Rep., 11, 234 (2021)
- 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)
- 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)
- F.Scala, E.Fattorusso, M.Menna, O.Taglialatela-Scafati, M.Tierney, M.Kaiser, D.Tasdemir. Mar. Drugs, 8, 2162 (2010)
- D.T.Mahajan, V.H.Masand, K.N.Patil, T.B.Hadda, V.Rastija. Med. Chem. Res., 22, 2284 (2013)
- R.D.Charan, G.Schlingmann, V.S.Bernan, X.Feng, G.T.Carter. J. Nat. Prod., 69, 29 (2006)
- 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)
- 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)
- A.Diaz, J.M.Vasquez Vallejo, A.Martinez Duran. J. Res. Develop., 25, 42 (1981)
- M.Harjo, M.Järvekülg, T.Tamm, T.F.Otero, R.Kiefer. PLoS ONE, 15, e0232851 (2020)
- 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)
- 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)
- 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)
- Z.Wang, M.Liang, H.Dong, P.Gao, Y.Su, P.Cai, S.Ding, J.Chen, S.Xue. Org. Lett., 19, 3711 (2017)
- 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)
- 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)
- P.Gómez, M.Más-Montoya, I.da Silva, J.P.Cerón-Carrasco, A.Tárraga, D.Curiel. Cryst. Growth Des., 17, 3371 (2017)
- H.Zhang, Z.Iqbal, Z-E.Chen, Yan-P.Hong. RSC Adv., 7, 35598 (2017)
- 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)
- 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)
- R.Domínguez, N.F.Montcada, P.de la Cruz, E.Palomares, F.Langa. ChemPlusChem, 82, 1096 (2017)
- M.Krzeszewski, D.Gryko, D.T.Gryko. Acc. Chem. Res., 50, 2334 (2017)
- S.Sugiura, H.Maeda. Org. Biomol. Chem., 18, 4433 (2020)
- B.A.Paulraj, P.Murugesan, A.V.Swaminathan, J.Madhavan, V.S.Rajadurai, P.M.Johnson. Comput. Mater. Sci., 162, 359 (2019)
- J.Chen, A.Burghart, A.Derecskei-Kovacs, K.Burgess. J. Org. Chem., 65, 2900 (2000)
- M.Albrecht, A.Lippach, M.P.Exner, J.Jerbi, M.Springborg, N.Budisa, G.Wenz. Org. Biomol. Chem., 13, 6728 (2015)
- 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)
- M.Poddar, R.Misra. Coord. Chem. Rev., 421, 213462 (2020)
- H.Lu, Z.Shen. Front. Chem., 8, 290 (2020)
- B.Matarranz, G.Fernández. Chem. Phys. Rev., 2, 041304 (2021)
- L.Yuan, W.Lin, K.Zheng, L.He, W.Huang. Chem. Soc. Rev., 42, 622 (2013)
- B.Bertrand, K.Passador, C.Goze, F.Denat, E.Bodio, M.Salmain. Coord. Chem. Rev., 358, 108 (2018)
- A.Turksoy, D.Yildiz, E.U.Akkaya. Coord. Chem. Rev., 379, 47 (2019)
- T.Zhang, C.Ma, T.Sun, Z.Xie. Coord. Chem. Rev., 390, 76 (2019)
- V.Lakshmi, R.Sharma, M.Ravikanth. Rep. Org. Chem., 6, 1 (2016)
- T.Kowad, H.Maeda, K.Kikuchi. Chem. Soc. Rev., 44, 4953 (2015)
- 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)
- 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)
- 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)
- 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)
- 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)
- Patent RU 2717308C1 (2019)
- 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)
- H.Wang, W.Zhao, X.Liu, S.Wang, Y.Wang. ACS Appl. Bio Mater., 3, 593 (2020)
- 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)
- 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)
- 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)
- G.Gupta, Y.Sun, A.Das, P.J.Stang, C.Y.Lee. Coord. Chem. Rev., 452, 214308 (2022)
- S.Kusaka, R.Sakamoto, Y.Kitagawa, M.Okumura, H.Nishihara. Chem. – Asian J., 7, 907 (2012)
- S.Erten-Ela, O.Vakuliuk, A.Tarnowska, K.Ocakoglu, D.T.Gryko. Spectrochim. Acta, Part A, 135, 676 (2015)
- O.Miguel, P.Zúñiga, Á.G.Sathicq, J.Jobanny, M.Zambrano, G.P.Romanelli. Cur. Org. Synt., 14, 1 (2017)
- M.Leonardi, V.Estévez, M.Villacampa, J.C.Menéndez. Synthesis, 51, 816 (2019)
- I.V.Efimov, L.N.Kulikova, A.R.Miftyakhova, M.D.Matveeva, L.G.Voskressensky. Chemistry Select., 6, e202103486 (2021)
- E.Abele, E.Lucevics. Heterocycles, 53, 2285 (2000)
- 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
- 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
- Z.Rappoport, J.F.Liebman. In The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids (Chichester: Wiley, 2008). P. 241
- Z.Wang. In Comprehensive Organic Name Reactions and Reagents. Pt 3. Paragraph 626 (London: Wiley, 2009)
- 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)
- 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)
- 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)
- 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)
- 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)
- E.Yu.Schmidt, A.I.Mikhaleva, A.M.Vasil’tsov, A.B.Zaitsev, N.V.Zorina. ARKIVOC, vii, 11 (2005)
- 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)
- A.M.Vasil’tsov, A.V.Ivanov, A.I.Mikhaleva, B.A.Trofimov. Tetrahedron Lett., 51, 1690 (2010)
- B.A.Trofimov, A.V.Ivanov, E.Yu.Schmidt, A.I.Mikhaleva. Chem. Heterocycl. Compd., 46, 762 (2010)
- S.E.Korostova, A.I.Mikhaleva, L.N.Sobenina, S.G.Shevchenko, R.I.Polovnikova. Zh. Org. Khim., 3, 492 (1986)
- A.I.Mikhaleva, B.A.Trofimov, A.N.Vasil’ev, G.A.Komarova, V.I.Skorobogatova. Chem. Heterocycl. Compd., 18, 920 (1982)
- B.A.Trofimov, A.I.Mikhaleva. Izv. ANauk SSSR. Ser. Khim., 12, 2840 (1979)
- B.A.Trofimov, A.I.Mikhaleva, A.V.Ivanov, V.S.Shcherbakova, I.A.Ushakov. Tetrahedron, 71, 124 (2015)
- A.V.Ivanov, V.S.Shcherbakova, A.I.Mikhaleva, B.A.Trofimov. Russ. J. Org. Chem., 50, 1775 (2014)
- A.V.Ivanov, V.S.Barnakova, A.I.Mikhaleva, B.A.Trofimov. Russ. Chem. Bull., 62, 2557 (2013)
- A.Yu.Kritskaya, N.A.Bumagina, E.V.Antina, A.A.Ksenofontov, M.B.Berezin,·A.S.Semeikin. J. Fluoresc., 28, 393 (2018)
- K.S.Rodygin, G.Werner, F.A.Kucherov, V.P.Ananikov. Chem. – Asian J., 11, 965 (2016)
- R.Fu, Z.Li, L.Gao. Prog. Chem., 31, 1303 (2019)
- D.A.Shabalin, A.Yu.Dubovtsev, E.Yu.Schmidt, B.A.Trofimov. Chem. Select., 5, 3434 (2020)
- N.Kaewchangwat, R.Sukato, V.Vchirawongkwin, T.Vilaivan, M.Sukwattanasinitt, S.Wacharasindhu. Green Chem., 17, 460 (2015)
- L.Ran, Z.-H.Ren, Y.-Y.Wang, Z.-H.Guan. Green Chem., 16, 112 (2014)
- Y.Xie, Y.Li, X.Chen, Y.Liua, W.Zhang. Org. Chem. Front., 5, 1698 (2018)
- Z.Xu, N.Xian, H.Chen, G.-J.Deng, H.Huang. Chin. J. Chem., 39, 1175 (2021)
- X.Tang, L.Huang, C.Qi, W.Wu, H.Jiang. Chem. Commun., 49, 9597 (2013)
- H.-B.Yang, N.Selander. Chem. – Eur. J., 23, 1779 (2017)
- K.Singh, M.Vellakkaran, D.Banerjee. Green Chem., 20, 2250 (2018)
- J.Wang, M.Tang, W.Gu, S.Huang, L.-G.Xie. J. Org Chem., 87, 12482 (2022)
- B.A.Shainyan. Russ. Chem. Rev., 91 (9), RCR5052 (2022)
- J.Vaitla, A.Bayer, K.H.Hopmann. Angew. Chem., Int. Ed., 56, 1 (2017)
- D.Chang, J.Chen, Y.Liu, H.Huang, A.Qin, G.-J.Deng. J. Org. Chem., 86, 110 (2021)
- T.T.Dang, A.M.Seayad. Chem. – Asian. J., 12, 2383 (2017)
- X.Wu, K.Li, S.Wang, C.Liu, A.Lei. Org. Lett., 18, 56 (2016)
- M.Fatahpour, N.Hazeri, M.T.Maghsoodlou, M.Lashkari. J. Iranian Chem. Soc., 16, 111 (2019)
- M.T.Huggins, T.Kesharwani, J.Buttrick, C.Nicholson. J. Chem. Educ., 97, 1425 (2020)
- M.J.Kim, S. M.Gaube, M.H.R.Beh, C.D.Smith, A.Thompson. RSC Adv., 9, 31773 (2019)
- G.Fang, J.Liu, J.Fu, Q.Liu, X.Bi. Org. Lett., 19, 1346 (2017)
- X.Jiang, T.Zhang, C.Sun, Y.Meng, L.Xiao. Chin. Chem. Lett., 30, 1055 (2019)
- A.F.Khlebnikov, O.A.Tomashenko, L.D.Funt, M.S.Novikov. Org. Biomol. Chem., 12, 6598 (2014)
- A.V.Galenko, A.F.Khlebnikov, M.S.Novikov, M.S.Avdontceva. Tetrahedron, 71, 1940 (2015)
- W.Wu, S.Wen, X.Zhang, Q.Lin, Z.Weng. Org. Lett., 23, 6352 (2021)
- J.Chen, C.Li, Y.Zhou, C.Sun, T.Sun. ChemCatChem., 11, 1943 (2019)
- Patent WO 2017002849 (2017)
- E.Vessally. RSC Adv., 6, 18619 (2016)
- S.Arshadi, E.Vessally, L.Edjlali, E.Ghorbani-Kalhor, R.Hosseinzadeh-Khanmiri. RSC Adv., 7, 13198 (2017)
- G.Cheng, W.Lv, L.Xue. Green Chem., 20, 4414 (2018)
- B.Ge, W.Lv, J.Yu, S.Xiao, G.Cheng. Org. Chem. Front., 5, 3103 (2018)
- N.Kanova, B.A.Dundar, Y.Kelgokmen, M.Zora. J. Org. Chem., 86, 6289 (2021)
- Q.Zhen, R.Li, L.Qi, K.Hu, X.Yao, Y.Shao. J. Chen. Org. Chem. Front., 7, 286 (2020)
- H.Liu, C.Qi, L.Wang, Y.Guo, D.Li, H. Jiang. J. Org. Chem., 86, 9610 (2021)
- B.A.Trofimov, A.I.Michaleva, E.Yu.Shmidt, L.N.Sobenina. Adv. Heterocycl. Chem., 209, 99 (2010)
- B.Eftekhari-Sis, M.Zirak, A.Akbari. Chem. Rev., 113, 2958 (2013)
- R.Javahershenas, F.M.Arlan, R.H.Prager, J.Khalafy. ARKIVOC, i, 117 (2020)
- X.Chang, X.Yang, Z.Chen, W.Zhong. Synlett, 30, 1431 (2019)
- F.Nezhad-Shahrokhabadi, M.Anary-Abbasinejad. J. Iran Chem. Soc., 19, 2655 (2022)
- M.Anary-Abbasinejada, F.Nezhad-Shahrokhabadi, M.Mohammadi. Mol. Divers., 24, 1205 (2020)
- N.N.Kolos, V.V.Zubar, I.V.Omelchenko, V.I.Musatov. Chem. Heterocycl. Compd., 52, 237 (2016)
- P.K.Shirsat, N.B.Khomane, P.R.Mali, R.R.Maddi, J.B.Nanubolu, H.M.Meshram. Chem. Select., 2, 11218 (2017)
- S.Das. RSC Adv., 18, 18875 (2020)
- 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)
- 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)
- L.Kurti. Appications of Named Reactions in Organic Synthesis. (Ed. B.Czako). (Elsevier, 2005). 864 p.
- J.Luo, D.Lu, Y.Peng, Q.Tang. Asian J. Org. Chem., 6, 1546 (2017)
- L.Hu, J.Luo, D.Lu, Q.Tang. Tetrahedron Lett., 59, 1698 (2018)
- V.Rajeshkumar, C.Neelamegam, S.Anandan. Synthesis, 51, 4023 (2019)
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