5-Chloro-4-formylpyrrole-3-carboxylates react with anilines or β-naphthylamine when heated in DMF under reflux to form ethyl pyrrolo[2,3-b]quinoline-3-carboxylates or their benzo[f] analogs, which exhibit moderate fluorescent properties. The corresponding carboxylic acids were obtained by alkaline hydrolysis of the synthesized carboxylates.
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Larghi, E. L.; Bracca, A. B. J.; Aguilar, A. A. A.; Heredia, D. A.; Pergomet, J. L.; Simonetti, S. O.; Kaufman, T. S. Curr. Top. Med. Chem. 2017, 15, 1683.
Trost, B. M.; Osipov, M. Chem.–Eur. J. 2015, 21, 16318.
Straight, A. F.; Cheung, A.; Limouze, J.; Chen, I.; Westwood, N. J.; Sellers, J. R.; Mitchison, T. J. Science 2003, 299, 1743.
Allingham, J. S.; Smith, R.; Rayment, I. Nat. Struct. Mol. Biol. 2005, 12, 378.
Lee, B. D.; Li, Z.; French, K. J.; Zhuang, Y.; Xia, Z.; Smith, C. D. J. Med. Chem. 2004, 47, 1413.
Lee, B. D.; French, K. J.; Zhuang, Y.; Smith, C. D. Oncol. Res. 2003, 14, 49.
Gakh, A.; Krasavin, M.; Karapetian, R.; Rufanov, K.; Konstantinov, I.; Godovykh, E.; Soldatkina, O.; Sosnov, A. US Patent 20138420815 B1.
Tanaka, T.; Iwakuma, T.; Wagatsuma, M.; Iijima, I. J. Heterocycl. Chem. 1972, 9, 1355.
Khan, M. A.; da Rocha, J. F. Heterocycles 1977, 6, 1229.
Murugesan, M.; Soundararajan, N.; Ramasamy, K.; Shanmugam, P. Synthesis 1979, 352.
Murugesan, M.; Ramasamy, K.; Shanmugam, P. Zeitsch. Naturforsch. B 1980, 35, 746.
Jin, H.; Tian, B.; Song, X.; Хie, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 12688.
Richter, R.; Ulrich, H. J. Org. Chem. 1973, 38, 2614.
Smith, L.; Kiselyov, A. S. Tetrahedron Lett. 1999, 40, 5643.
Himbert, G.; Schwickerath, W.; Maas, G. Liebigs Ann. Chem. 1985, 1389.
Zeng, Z.; Jin, H.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2018, 57, 16549.
Hsu, Y.-C.; Hsieh, S.-A.; Liu, R. S. Chem.–Eur. J. 2019, 25, 5288.
Molina, P.; Alcántara, J.; López-Leonardo, C. Tetrahedron 1997, 53, 3281.
Saito, T.; Furukawa, N.; Otani, T. Org. Biomol. Chem. 2010, 8, 1126.
Zhao, H.; Xing,Y.; Lu, P.; Wang, Y. Chem.–Eur. J. 2016, 22, 15144.
Chen, K.; Tang, X.-Y.; Shi, M. Chem. Commun. 2016, 52, 1967.
Metten, B.; Kostermans, M.; Van Baelen, G.; Smet, M.; Dehaen, W. Tetrahedron 2006, 62, 6018.
Grozav, A. N; Fedoriv, M. Z.; Chornous, V. A.; Palamar, A. A.; Bratenko, M. K.; Vovk, M. V. Chem. Heterocycl. Compd. 2019, 55, 435. [Khim. Geterotsikl. Soedin. 2019, 55, 435.]
Brack, A. Liebigs Ann. 1965, 681, 105.
Rurack, K.; Danel, A.; Rotkiewicz, K.; Grabka, D.; Spieles, M.; Rettig, W. Org. Lett. 2002, 4, 4647.
Funaki, J.; Imai, K.; Araki, K.; Danel, A.; Tomasik, P. Pol. J. Chem. 2004, 78, 843.
Wan, W.; Wang, H.; Lin, H.; Wang, J.; Jiang, Y.; Jiang, H.; Zhu, S.; Wang, Z.; Hao, J. Dyes Pigm. 2015, 121, 138.
Metten, B.; Smet, M., Boens, N.; Dehaen, W. Synthesis 2005, 1838.
Całus, S.; Gondek, E.; Danel, A.; Jarosz, B. Pokładko, M.; Kityk, A. V. Mater. Lett. 2007, 61, 3292.
Całus, S.; Gondek, E.; Danel, A.; Jarosz, B.; Kityk, A. V. Opt. Commun. 2007, 271, 16.
Gondek, E.; Danel, A.; Niziol, J.; Armatys, P.; Kityk, I. V.; Szlacheic, P.; Korelus, M.; Uchacz, T.; Chmast, J. Opt. Commun. 2007, 277, 16.
Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer, 2006, 3rd ed., p. 5.
Jones, G.; Jackson, W. R.; Choi, C. Y.; Bergmark, W. R. J. Phys. Chem. 1985, 89, 294.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2008, A64, 112.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(10), 1024–1030
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Grozav, A.N., Fedoriv, M.Z., Chornous, V.А. et al. Cyclocondensation of 5-chloro-4-formylpyrrole-3-carboxylates with arylamines. Synthesis and fluorescent properties of pyrrolo[2,3-b]quinoline-3-carboxylates and their benzo[f] analogs. Chem Heterocycl Comp 57, 1024–1030 (2021). https://doi.org/10.1007/s10593-021-03017-y
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DOI: https://doi.org/10.1007/s10593-021-03017-y