The reactions of quinoline-2(6,8)-carbaldehydes with arenes by the action of strong Brønsted (H2SO4, CF3SO3H) or Lewis (AlCl3, AlBr3) acids led to the formation of substituted diarylmethylquinolines in high yields.
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Achan, J.; Talisuna, A. O.; Erhart, A.; Yeka, A.; Tibenderana, J. K.; Baliraine, F. N.; Rosenthal, P. J.; D’Alessandro, U. Malar. J. 2011, 10, 144.
Samosorn, S.; Bremner, J. B.; Ball, A.; Lewis, K. Bioorg. Med. Chem. 2006, 14, 857.
Maignan, S.; Guilloteau, J.; Zhou-Liu, Q.; Clement-Mella, C.; Mikol, V. J. Mol. Biol. 1998, 282, 359.
Zouhiri, F.; Desmaele, D.; d’Angelo, J.; Ourevitch, M.; Mouscadet, J.-F.; Leh, H.; Le Bret, M. Tetrahedron Lett. 2001, 42, 8189.
McCormick, J. L.; McKee, T. C.; Cardellina II, J. H.; Boyd, M. R. J. Nat. Prod. 1996, 59, 469.
Yadav, D. K.; Rai, R.; Kumar, N.; Singh, S.; Misra, S.; Sharma, P.; Shaw, P.; Perez-Sanchez, H.; Mancera, R. L.; Choi, E. H.; Kim, M.-h.; Pratap, R. Sci. Rep. 2016, 6, article number 38128.
Matsuno, K.; Masuda, Y.; Uehara, Y.; Sato, H.; Muroya, A.; Takahashi, O.; Yokotagawa, T.; Furuya, T.; Okawara, T.; Otsuka, M.; Ogo, N.; Ashizawa, T.; Oshita, C.; Tai, S.; Ishii, H.; Akiyama, Y.; Asai, A. ACS Med. Chem. Lett. 2010, 1, 371.
Aly, R. M.; Serya, R. A. T.; El-Motwally, A. M.; Esmat, A.; Abbas, S.; El Ella, D. A. A. Bioorg. Chem. 2017, 75, 368.
Khusnutdinov, R. I.; Bayguzina, A. R.; Dzhemilev, U. M. J. Organomet. Chem. 2014, 768, 75.
Madapa, S.; Tusi, Z.; Batra, S. Curr. Org. Chem. 2008, 12, 1116.
Ryabukhin, D. S.; Vasilyev, A. V. Russ. Chem. Rev. 2016, 85, 637.
Njoroge, M.; Njuguna, N. M.; Mutai, P.; Ongarora, D. S. B.; Smith, P. W.; Chibale, K. Chem. Rev. 2014, 114, 11138.
Teixeira, C.; Vale, N.; Perez, B.; Gomes, A.; Gomes, J. R. B.; Gomes, P. Chem. Rev. 2014, 114, 11164.
Barnett, D. S.; Guy, R. K. Chem. Rev. 2014, 114, 11221.
Ryabukhin, D. S.; Zakusilo, D. N.; Kompanets, M. O.; Tarakanov, A. A.; Boyarskaya, I. A.; Artamonova, T. O.; Khohodorkovskiy, M. A.; Opeida, I. O.; Vasilyev, A. V. Beilstein J. Org. Chem. 2016, 12, 2125.
Klumpp, D. A.; Lau, S. J. Org. Chem. 1999, 64, 7309.
Prakash, G. K. S.; Paknia, F.; Chacko, S.; Mathew, T.; Olah, G. A. Heterocycles 2008, 76, 783.
Sheets, M. R.; Li, A.; Bower, E. A.; Weigel, A. R.; Abbott, M. P.; Gallo, R. M.; Mitton, A. A.; Klumpp, D. A. J. Org. Chem. 2009, 74, 2502.
Ryabukhin, D. S.; Turdakov, A. N.; Soldatova, N. S.; Kompanets, M. O.; Ivanov, A. Yu.; Boyarskaya, I. A.; Vasilyev, A. V. Beilstein J. Org. Chem. 2019, 15, 1962.
Klumpp, D. A.; Kindelin, P. J.; Li, A. Tetrahedron Lett. 2005, 46, 2931.
Gurskaya, L. Y.; Belyanskaya, D. S.; Ryabukhin, D. S.; Nilov, D. I.; Boyarskaya, I. A.; Vasilyev, A. V. Beilstein J. Org. Chem. 2016, 12, 950.
Klumpp, D. A.; Jones, A.; Lau, S.; de Leon, S.; Garza, M. Synthesis 2000, 1117.
This work was supported by the Russian Foundation for Basic Research (grant 20-03-00074).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 964–967
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Borisova, M.А., Ryabukhin, D.S. & Vasilyev, A.V. Reactions of quinoline-2(6,8)-carbaldehydes with arenes by the action of various Brønsted or Lewis acids: synthesis of diarylmethylquinolines. Chem Heterocycl Comp 56, 964–967 (2020). https://doi.org/10.1007/s10593-020-02759-5
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DOI: https://doi.org/10.1007/s10593-020-02759-5