This review article describes methods for the preparation of pyrrolo[1,2-a]quinoxalines, covering literature sources from the last 10 years. The attention was largely paid to new, original methods for the synthesis of pyrrolo[1,2-a]-quinoxalines on the basis of pyrrole and quinoxaline derivatives, as well as multicomponent reactions leading to the formation of both pyrrole and quinoxaline rings.
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Huang, A.; Ma, C. Mini-Rev. Med. Chem. 2013, 13, 607.
(a) Ronga, L.; Del Favero, M.; Cohen, A.; Soum, C.; Le Pape, P.; Savrimoutou, S.; Pinaud, N.; Mullie, C.; Daulouede, S.; Vincendeau, P.; Farvacques, N.; Agnamey, P.; Pagniez, F.; Hutter, S.; Azas, N.; Sonnet, P.; Guillon, J. Eur. J. Med. Chem. 2014, 81, 378. (b) van Heerden, L.; Cloete, T. T.; Breytenbach, J. W.; de Kock, C.; Smith, P.; Breytenbach, J. C.; N'Da, D. D. Eur. J. Med. Chem. 2012, 55, 335. (c) Guillon, J.; Mouray, E.; Moreau, S.; Mullie, C.; Forfar, I.; Desplat, V.; Belisle-Fabre, S.; Pinaud, N.; Ravanello, F.; Le-Naour, A.; Leger, J.-M.; Gosmann, G.; Jarry, C.; Deleris, G.; Sonnet, P.; Grellier, P. Eur. J. Med. Chem. 2011, 46, 2310. (d) Jonet, A.; Guillon, J.; Mullie, C.; Cohen, A.; Bentzinger, G.; Schneider, J.; Taudon, N.; Hutter, S.; Azas, N.; Moreau, S.; Savrimoutou, S.; Agnamey, P.; Dassonville-Klimpt, A.; Sonnet, P. Med. Chem. 2018, 14, 293. (e) Guillon, J.; Cohen, A.; Gueddouda, N. M.; Das, R. N.; Moreau, S.; Ronga, L.; Savrimoutou, S.; Basmaciyan, L.; Monnier, A.; Monget, M.; Rubio, S.; Garnerin, T.; Azas, N.; Mergny, J.-L.; Mullie, C.; Sonnet, P. J. Enzyme Inhib. Med. Chem. 2017, 32, 547.
Xu, H.; Fan, L.-L. Eur. J. Med. Chem. 2011, 46, 1919.
Morelli, E.; Gemma, S.; Budriesi, R.; Campiani, G.; Novellino, E.; Fattorusso, C.; Catalanotti, B.; Coccone, S. S.; Ros, S.; Borrelli, G.; Kumar, V.; Persico, M.; Fiorini, I.; Nacci, V.; Ioan, P.; Chiarini, A.; Hamon, M.; Cagnotto, A.; Mennini, T.; Fracasso, C.; Colovic, M.; Caccia, S.; Butini, S. J. Med. Chem. 2009, 52, 3548.
(a) Guillon, J.; Le Borgne, M.; Rimbault, C.; Moreau, S.; Savrimoutou, S.; Pinaud, N.; Baratin, S.; Marchivie, M.; Roche, S.; Bollacke, A.; Pecci, A.; Alvarez, L.; Desplat, V.; Jose, J. Eur. J. Med. Chem. 2013, 65, 205. (b) Desplat, V.; Moreau, S.; Gay, A.; Fabre, S. B.; Thiolat, D.; Massip, S.; Macky, G.; Godde, F.; Mossalayi, D.; Jarry, C.; Guillon, J. J. Enzyme Inhib. Med. Chem. 2010, 25, 204.
Connell, P.; Lv, W.; Budke, B.; Kozikowski, A. WO Patent 2017149493A1; Сhem. Аbstr. 2017, 167, 348866.
Brindisi, M.; Brogi, S.; Maramai, S.; Grillo, A.; Borrelli, G.; Butini, S.; Novellino, E.; Allara, M.; Ligresti, A.; Campiani, G.; Di Marzo, V.; Gemma, S. RSC. Adv. 2016, 6, 64651.
Sanchez Alonso, P.; Alajarin Ferrandez, R.; Vaquero Lopez, J. J.; Rodriguez Puyol, M.; Griera Merino, M.; Diez Marques, M. L.; Rodriguez Puyol, D. ES Patent 2522717; Сhem. Аbstr. 2016, 164, 314943.
Mashevskaya, I. V.; Kislina, L. V.; Makhmudov, R. R.; Maslivets, A. N. RU Patent 2471798; Сhem. Аbstr. 2013, 158, 131774.
(a) Desplat, V.; Vincenzi, M.; Lucas, R.; Moreau, S.; Savrimoutou, S.; Pinaud, N.; Lesbordes, J.; Peyrilles, E.; Marchivie, M.; Routier, S.; Sonnet, P.; Rossi, F.; Ronga, L.; Guillon, J. Eur. J. Med. Chem. 2016, 113, 214. (b) Desplat, V.; Vincenzi, M.; Lucas, R.; Moreau, S.; Savrimoutou, S.; Rubio, S.; Pinaud, N.; Bigat, D.; Enriquez, E.; Marchivie, M.; Routier, S.; Sonnet, P.; Rossi, F.; Ronga, L.; Guillon, J. ChemMedChem 2017, 12, 940.
Wang, T.; Tang, Y.; Yang, Y.; An, Q.; Sang, Z.; Yang, T.; Liu, P.; Zhang, T.; Deng, Y.; Luo, Y. Bioorg. Med. Chem. Lett. 2018, 28, 2084.
Gemma, S.; Colombo, L.; Forloni, G.; Savini, L.; Fracasso, C.; Caccia, S.; Salmona, M.; Brindisi, M.; Joshi, B. P.; Tripaldi, P.; Giorgi, G.; Taglialatela-Scafati, O.; Novellino, E.; Fiorini, I.; Campiani, G.; Butini, S. Org. Biomol. Chem. 2011, 9, 5137.
(a) Kalinin, A. A.; Mamedov, V. A. Chem. Heterocycl. Compd. 2011, 46, 1423. [Khim. Geterotsikl. Soedin. 2010, 1763.] (b) Mamedov, V. A.; Kalinin, A. A. Chem. Heterocycl. Compd. 2010, 46, 641. [Khim. Geterotsikl. Soedin. 2010, 803.]
He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451.
Zhang, Z.; Li, J.; Zhang, G.; Ma, N.; Liu, Q.; Liu, T. J. Org. Chem. 2015, 80, 6875.
Schulte, A.; Situ, X.; Saito, S.; Wunsch, B. Chirality 2014, 26, 793.
Potikha, L. M.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2009, 45, 1396. [Khim. Geterotsikl. Soedin. 2009, 1734.]
An, Z.; Zhao, L.; Wu, M.; Ni, J.; Qi, Z.; Yu, G.; Yan, R. Chem. Commun. 2017, 53, 11572.
An, Z.; Jiang, Y.; Guan, X.; Yan, R. Chem. Commun. 2018, 54, 10738.
(a) Zhang, Z.; Xie, C.; Tan, X.; Song, G.; Wen, L.; Gao, H.; Ma, C. Org. Chem. Front. 2015, 2, 942. (b) Mani, G. S.; Subba Rao, A. V.; Tangella, Y.; Sunkari, S.; Sultana, F.; Namballa, H. K.; Shankaraiah, N.; Kamal, A. New J. Chem. 2018, 42, 15820.
Reddy, L. M.; Reddy, V. V.; Putta, C. S.; Satteyyanaidu, V.; Reddy, C. K.; Subba Reddy, B. V. ChemistrySelect 2018, 3, 9881.
Li, J.; Zhang, J.; Yang, H.; Gao, Z.; Jiang, G. J. Org. Chem. 2017, 82, 765.
(a) Ramamohan, M.; Sridhar, R.; Raghavendrarao, K.; Paradesi, N.; Chandrasekhar, K. B.; Jayaprakash, S. Synlett 2015, 1096. (b) Wang, C.; Li, Y.; Guo, R.; Tian, J.; Tao, C.; Cheng, B.; Wang, H.; Zhang, J.; Zhai, H. Asian J. Org. Chem. 2015, 4, 866.
(a) Lade, J. J.; Patil, B. N.; Sathe, P. A.; Vadagaonkar, K. S.; Chetti, P.; Chaskar, A. C. ChemistrySelect 2017, 2, 6811. (b) Lade, J. J.; Patil, B. N.; Vhatkar, M. V.; Vadagaonkar, K. S.; Chaskar, A. C. Asian J. Org. Chem. 2017, 6, 1579. (c) Liu, H.; Zhou, F.; Luo, W.; Chen, Y.; Zhang, C.; Ma, C. Org. Biomol. Chem. 2017, 15, 7157.
Dai, C.; Deng, S.; Zhu, Q.; Tang, X. RSC Adv. 2017, 7, 44132.
(a) Kamal, A.; Babu, K. S.; Kovvuri, J.; Manasa, V.; Ravikumar, A.; Alarifi, A. Tetrahedron Lett. 2015, 56, 7012. (b) Singh, D. K.; Nath, M. Beilstein J. Org. Chem. 2014, 10, 808. (c) Wang, C.; Li, Y.; Zhao, J.; Cheng, B.; Wang, H.; Zhai, H. Tetrahedron Lett. 2016, 57, 3908. (d) Krishna, T.; Reddy, T. N.; Laxminarayana, E.; Kalita, D. ChemistrySelect 2019, 4, 250.
(a) Huo, H.-R.; Tang, X.-Y.; Gong, Y.-F. Synthesis 2018, 2727. (b) Verma, A. K.; Jha, R. R.; Sankar, V. K.; Aggarwal, T.; Singh, R. P.; Chandra, R. Eur. J. Org. Chem. 2011, 6998. (c) Preetam, A.; Nath, M. RSC Adv. 2015, 5, 21843.
(a) Rashidi, R.; Nasr-Esfahani, M.; Mohammadpoor-Baltork, I.; Tangestaninejad, S.; Moghadam, M.; Mirkhani, V. Monatsh. Chem. 2018, 149, 557. (b) Li, Y.; Su, Y.-H.; Dong, D.-J.; Wu, Z.; Tian, S.-K. RSC Adv. 2013, 3, 18275.
Maiti, B.; Sun, Ch.-M. New J. Chem. 2011, 35, 1385.
(a) Liu, G.; Zhou, Y.; Lin, D.; Wang, J.; Zhang, L.; Jiang, H.; Liu, H. ACS Comb. Sci. 2011, 13, 209. (b) Patil, N. P.; Lakshmi, P. G. V. V.; Singh, V. Eur. J. Org. Chem. 2010, 4719. (c) Patil, N. T.; Kavthe, R. D.; Raut, V. S.; Reddy, V. V. J. Org. Chem. 2009, 74, 6315.
Xie, C.; Zhang, Z.; Li, D.; Gong, J.; Han, X.; Liu, X.; Ma, C. J. Org. Chem. 2017, 82, 3491.
Pereira, M. de F.; Thiery, V. Org. Lett. 2012, 14, 4754.
Liu, H.; Duan, T.; Zhang, Z.; Xie, C.; Ma, C. Org. Lett. 2015, 17, 2932.
(a) Li, Z.; Yan, N.; Xie, J.; Liu, P.; Zhang, J.; Dai, B. Chin. J. Chem. 2015, 33, 589. (b) Jiang, Z.; Zhang, J.; Tong, Y.; Shi, X.; Miao, D.; Han, S. Chin. J. Org. Chem. 2014, 34, 1845.
Ammermann, S.; Hrib, Ch.; Jones, P. G.; du Mont, W.-W.; Kowalsky, W.; Johannes, H.-H. Org. Lett. 2012, 14, 5090.
Mamedov, V. A.; Khafizova, E. A.; Zamaletdinova, A. I.; Voronina, J. K.; Kadyrova, S. F.; Mironova, E. V.; Krivolapov, D. B.; Rizvanov, I. Kh.; Sinyashin, O. G. Chem. Heterocycl. Compd. 2017, 53, 560. [Khim. Geterotsikl. Soedin. 2017, 53, 560.]
Mashevskaya, I. V.; Mokrushin, I. G.; Bozdyreva, K. S.; Maslivets, A. N. Russ. J. Org. Chem. 2011, 47, 253. [Zh. Org. Khim. 2011, 47, 261.]
(a) Keivanloo, A.; Kazemi, S. S.; Nasr-Isfahani, H.; Bamoniri, A. Tetrahedron 2016, 72, 6536. (b) Keivanloo, A.; Soozani, A.; Bakherad, M.; Mirzaee, M.; Rudbari, H. A.; Bruno, G. Tetrahedron 2017, 73, 1633.
Wang, M.; Liu, C.; Gu, Y. Tetrahedron 2016, 72, 6854.
(a) Moradi, L.; Piltan, M.; Abasi, G. Helv. Chim. Acta 2014, 97, 646. (b) Sanaeishoar, T.; Adibi-Sedeh, S.; Karimian, S. Comb. Chem. High Throughput Screening 2014, 17, 157.
(a) Piltan, M. J. Chem. Res. 2016, 40, 410. (b) Piltan, M.; Moradi, L.; Abasi, G.; Zarei, S. A. Beilstein J. Org. Chem. 2013, 9, 510.
Piltan, M. Chin. Chem. Lett. 2014, 25, 1507.
(a) Nicolescu, A.; Deleanu, C.; Georgescu, E.; Georgescu, F.; Iurascu, A.-M.; Shova, S.; Filip, P. Tetrahedron Lett. 2013, 54, 1486. (b) Georgescu, E.; Nicolescu, A.; Georgescu, F.; Teodorescu, F.; Shova, S.; Marinoiu, A. T.; Dumitrascu, F.; Deleanu, C. Tetrahedron 2016, 72, 2507. (c) Georgescu, E.; Nicolescu, A.; Georgescu, F.; Shova, S.; Toedorescu, F.; Macsim, A.-M.; Deleanu, C. Synthesis 2015, 1643.
(a) Georgescu, E.; Nicolescu, A.; Georgescu, F.; Teodorescu, F.; Marinescu, D.; Macsim, A.-M.; Deleanu, C. Beilstein J. Org. Chem. 2014, 10, 2377. (b) Moldoveanu, C.; Zbancioc, G.; Mantu, D.; Maftei, D.; Mangalagiu, I. PLoS One 2016, 11, e0156129.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 584–597
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Kalinin, A.A., Islamova, L.N. & Fazleeva, G.M. New achievements in the synthesis of pyrrolo[1,2-a]quinoxalines. Chem Heterocycl Comp 55, 584–597 (2019). https://doi.org/10.1007/s10593-019-02501-w
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DOI: https://doi.org/10.1007/s10593-019-02501-w