Abstract
The synthesis of quinoline derivatives through bismuth-catalyzed cyclization of phenylacetylene with ethyl 2-(arylimino)acetates has been reported. The excellence of this method is that the reaction is carried out at room temperature, and the catalyst is exceptionally productive, low toxic, and very cheap. The mild reaction conditions added an extraordinary benefit and made it attractive in economic and environmental aspects. The target products were isolated in up to 89% yield.
REFERENCES
Michael, J.P., Nat. Prod. Rep., 2008, vol. 25, p.166. https://doi.org/10.1039/B612168N
Solomon, R.V. and Lee, H., Curr. Med. Chem., 2011, vol. 18, p. 1488. https://doi.org/10.2174/092986711795328382
Bax, B.D., Chan, P.F., Eggleston, D.S., Fosberry, A., Gentry, D.R., Gorrec, F., Giordano, I., Hann, M.M., Hennessy, A., Hibbs, M., Huang, J., Jones, E., Jones, J., Brown, K.K., Lewis, C.J., May, E.W., Saunders, M.R., Singh, O., Spitzfaden, C.E., Shen, C., Shillings, A., Theobald, A.J., Wohlkonig, A., Pearson, N.D., and Gwynn, M.N., Nature, 2010, vol. 466, no. 7309, p. 935. https://doi.org/10.1038/nature09197
Carrigan, C.N., Esslinger, C.S., Bartlett, R.D., Bridges, R.J., and Thompson, C.M., Bioorg. Med. Chem. Lett., 1999, vol. 9, p. 2607. https://doi.org/10.1016/s0960-894x(99)00444-8
Carrigan, C.N., Bartlett, R.D., Esslinger, C.S., Cybulski, K.A., Tongcharoensirikul, P., Bridges, R.J., and Thompson, C.M., J. Med. Chem., 2002, vol. 45, p. 2260. https://doi.org/10.1021/jm010261z
Horchler, C.L., McCauley, J.P., Hall, J.E., Snyder, D.H., Moore, W.C., Hudzik, T.J., and Chapdelaine, M.J., Bioorg. Med. Chem., 2007, vol. 15, p. 939. https://doi.org/10.1016/j.bmc.2006.10.037
Zhu, Y.F., Wang, X.C., Connors, P., Wilcoxen, K., Gao, Y.H., Gross, R., Strack, N., Gross, T., McCarthy, J.R., Xie, Q., Ling, N., and Chen, C., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 1931. https://doi.org/10.1016/S0960-894X(03)00322-6
Zhang, Y. and Sigman, M.S., J. Am. Chem. Soc., 2007, vol. 129, p. 3076. https://doi.org/10.1021/ja070263u
Laras, Y., Hugues, V., Chandrasekaran, Y., Blanchard-Desce, M., Acher, F.C., and Pietrancosta, N., J. Org. Chem., 2012, vol. 77, p. 8294. https://doi.org/10.1021/jo301652j
Saburi, H., Tanaka, S., and Kitamura, M., Angew. Chem., Int. Ed., 2005, vol. 44, p. 1730. https://doi.org/10.1002/anie.200462513
Madapa, S., Tusi, Z., and Batra, S., Curr. Org. Chem., 2008, vol. 12, p. 1116. https://doi.org/10.2174/138527208785740300
Jia, X.-D., Peng, F.-F., Qing, C., Huo, C.-D., and Wang, X.-C., Org. Lett., 2012, vol. 14, p. 4030. https://doi.org/10.1021/ol301909g
Huo, C., Yuan, Y., Wu, M., Jia, X., Wang, X., Chen, F., and Tang, J., Angew. Chem., Int. Ed., 2014, vol. 53, p. 13544. https://doi.org/10.1002/anie.201406905
Wang, C., Ding, Q., Zheng, Q., Bao, P., and Peng, Y., Tetrahedron, 2018, vol. 74, no. 2, p. 348. https://doi.org/10.1016/j.tet.2017.12.004
Ni, M., Zhang, Y., Gong, T., and Feng, B., Adv. Synth. Catal., 2017, vol. 359, no. 5, p. 824. https://doi.org/10.1002/adsc.201601066
Leonard, N.M., Wieland, L.C., and Mohan, R.S., Tetrahedron, 2002, vol. 58, p. 8373. https://doi.org/10.1016/S0040-4020(02)01000-1
ACKNOWLEDGMENTS
The authors thank the Central Instrumentation Facility (CIF, Pondicherry University) for the NMR spectroscopic facility and DST-FIST for the ESI-MS and single-crystal XRD facility. M.A.B.R. acknowledges Pondicherry University for providing University Research Fellowship.
Funding
T.S. thanks the Science and Engineering Research Board, Government of India, for financial support (file no. EEQ/2018/000428).
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Riyaz, M.A.B., Nimbus, L.C., Rajasekhar, B. et al. Synthesis of Substituted Quinolines through Bismuth-Catalyzed Cyclization. Russ J Org Chem 59, 150–157 (2023). https://doi.org/10.1134/S1070428023010165
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DOI: https://doi.org/10.1134/S1070428023010165