Abstract
An efficient procedure has been developed for the synthesis of ethyl (2E)-5-phenylpent-2-en-4-ynoate by olefination-dehydrohalogenation of (2Z)-2-iodo-3-phenylprop-2-enal prepared by iodination of commercially available cinnamaldehyde.
References
Mejia, E.J., Magranet, L.B., De Voogd, N.J., Ten-Dyke, K., Qiu, D., Shen, Y.Y., Zhou, Z., and Crews, P., J. Nat. Prod., 2013, vol. 76, p. 425. doi https://doi.org/10.1021/np3008446
Nussbaumer, P., Leitner, I., Mraz, K., and Stutz, A., J. Med. Chem., 1995, vol. 38, p. 1831. doi https://doi.org/10.1021/jm00010a029
Sunagatullina, A.S., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Gen. Chem., 2013, vol. 83, p. 148. doi https://doi.org/10.1134/S1070363213010313
Shakhmaev, R.N., Sunagatullina, A.Sh., Emyshaeva, N.V., and Zorin, V.V., Chem. Nat. Compd., 2015, vol. 51, p. 127. doi https://doi.org/10.1007/s10600-015-1217-8
Shakhmaev, R.N., Sunagatullina, A.Sh., Abdullina, E.A., and Zorin, V.V., Russ. J. Org. Chem., 2017, vol. 53, p. 1705. doi https://doi.org/10.1134/S1070428017110173
Deussen, H.-J., Jeppesen, L., Scharer, N., Junager, F., Bentzen, B., Weber, B., Weil, V., Mozer, S.J., and Sauerberg, P., Org. Process Res. Dev., 2004, vol. 8, p. 363. doi https://doi.org/10.1021/op034048j
Zanka, A., Uematsu, R., Morinaga, Y., Yasuda, H., and Yamazaki, H., Org. Process Res. Dev., 1999, vol. 3, p. 389. doi https://doi.org/10.1021/op990044w
Takeuchi, R., Tanabe, K., and Tanaka, S., J. Org. Chem., 2000, vol. 65, p. 1558. doi https://doi.org/10.1021/jo991350a
Bates, C.G., Saejueng, P., and Venkataraman, D., Org. Zett., 2004, vol. 6, p. 1441. doi https://doi.org/10.1021/ol049706e
Krause, N., Chem. Ber., 1990, vol. 123, p. 2173. doi https://doi.org/10.1002/cber.19901231114
Kim, G., Lee, D.G., and Chang, S., Bull. Korean Chem. Soc., 2001, vol. 22, p. 943. doi https://doi.org/10.1002/chin.200216065
Lee, E.Y., Kim, Y., Lee, J.S., and Park, J., Eur. J. Org. Chem., 2009, p. 2943. doi https://doi.org/10.1002/ejoc.200900274
Kona, J.R., King’ondu, C.K., Howell, A.R., and Suib, S.L., ChemCatChem, 2014, vol. 6, p. 749. doi https://doi.org/10.1002/cctc.201300942
Ren, C., Shi, Z., Ding, W., Liu, Z., Jin, H., Yu, X., and Wang, S., Tetrahedron Lett., 2018, vol. 59, p. 14. doi https://doi.org/10.1016/j.tetlet.2017.09.020
Krafft, M.E. and Cran, J.W., Synlett, 2005, vol. 8, p. 1263. doi https://doi.org/10.1055/s-2005-868495
Hashmi, A.S.K., Häffner, T., Rudolph, M., and Rominger, F., Eur. J. Org. Chem., 2011, p. 667. doi https://doi.org/10.1002/ejoc.201001479
Blanchette, M.A., Choy, W., Davis, J.T., Essenfeld, A.P., Masamune, S., Roush, W.R., and Sakai, T., Tetrahedron Lett., 1984, vol. 25, p. 2183. doi https://doi.org/10.1016/S0040-4039(01)80205-7
Rathke, M.W. and Nowak, M., J. Org. Chem., 1985, vol. 50, p. 2624. doi https://doi.org/10.1021/jo00215a004
Sunagatullina, A.Sh., Shakhmaev, R.N., and Zorin, V.V, Russ. J. Org. Chem., 2013, vol. 49, p. 730. doi https://doi.org/10.1134/S1070428013050163
Funding
This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation in the framework of the base part of state assignment in the sphere of research activity (project no. 4.6451.2017/8.9).
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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 6, pp. 976–979.
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Shakhmaev, R.N., Sunagatullina, A.S., Ignatishina, M.G. et al. Synthesis of Ethyl (2E)-5-Phenylpent-2-en-4-ynoate. Russ J Org Chem 55, 897–899 (2019). https://doi.org/10.1134/S1070428019060253
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DOI: https://doi.org/10.1134/S1070428019060253