Abstract
C,C-Coupling of indole-3-carbaldehyde arylhydrazones with quinazoline in trifluoroacetic acid has occurred at position 5 or 7′ of the hydrazone molecule and has afforded the σ-adducts. The C,C-coupling has been accompanied by a change in the E-configuration of the C=N bond of the starting hydrazones to the Z-configuration in the formed quinazoline trifluoroacetyl hydrazides.
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REFERENCES
D’yakonov, A.L. and Telezhenetskaya, M.V., Khim. Prirod. Soedin., 1997, no. 33, p. 221.
Aniszewski, T., Alkaloids, Helsinki: Elsevier Sci., 2015.
Asif, M., Int. J. Med. Chem., 2014. Article ID 395637, p. 1.
Solyanik, G.I., Exp. Oncology, 2019, vol. 41, p. 3. https://doi.org/10.32471/exp-oncology.2312-8852.vol-41-no-1.12414
Tregubenko, I.P., Tarakhtii, E.A., Chibiryak, M.V., Golomolzin, B.V., and Egorova, L.G., Radiobiol., 1984, no. 24, p. 838.
Pilicheva, T.L., Chupakhin, O.N., and Postovsky, I.Ya., Chem. Heterocycl. Compd., 1975, no. 11, p. 561. https://doi.org/10.1007/BF00502444
Azev, Yu.A., Shorshnev, S.V., and Golomolzin, B.V., Tetrahedron Lett., 2009, vol. 50, p. 2899. https://doi.org/10.1016/j.tetlet.2009.03.199
Azev, Yu.A., Koptyaeva, O.S., Seliverstova, E.A., Ivoilova, A.V., and Pospelova, T.A., Russ. J. Gen. Chem., 2019, vol. 89, no. 12, p. 2374. https://doi.org/10.1134/S1070363219120089
Sundberg, R.J., Indoles, San Diego: Acad. Press Inc., 1996.
Chadra, N. and Silakari, O., Key Heterocycle Cores for Designing Multitargeting Molecules, Patiala: Elsevier, 2018, p. 285. https://doi.org/10.1016/B978-0-08-102083-8.00008-X
Anastas, P.T. and Warner, J.C., Green Chemistry Theory and Practice, New York: Oxford University Press, 1998, p. 516.
Charushin, V.N. and Chupakhin, O.N., Topics in Heterocyclic Chemistry, Switzerland: Springer, 2014, no. 37, p. 1.
Makosza, M. and Wojciechowski, K., Topics in Heterocyclic Chemistry, Switzerland: Springer, 2014, no. 37, p. 50.
Zabaleta, N., Uria, U., Reyes, E., Carrillo, L., and Vicario, J.L., Chem. Commun., 2018, vol. 54, p. 8905. https://doi.org/10.1039/C8CC05311A
Tung, T., Tezcan, H., San, M., Bueykguengoer, O., and Yagbasan, R., Acta Crystallogr. (C), 2003, vol. 59, p. 528. https://doi.org/10.1107/S0108270103016019
Kitaev, Yu.P. and Buzykin, B.I., Gidrazony (Hydrazones), Moscow: Nauka, 1974.
Jones, R.O., Rev. Mod. Phys., 2015, vol. 87, p. 897. https://doi.org/10.1103/RevModPhys.87.897
Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648. https://doi.org/10.1063/1.464913
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, Jr.J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision C. 01. Wallingford CT: Gaussian Inc., 2016.
Barilone, J. and Neese, F., Appl. Magn. Res., 2015, vol. 46, p. 117. https://doi.org/10.1007/s00723-014-0627-2
Neese, F., Wiley Interdiscip. Rev.: Comput. Mol. Sci., 2012, no. 2, p. 73. https://doi.org/10.1002/wcms.81
Stol, S. and Schweiger, A., J. Magn. Res., 2006, vol. 178, p. 42. https://doi.org/10.1016/j.jmr.2005.08.013
König, W., Ber., 1911, vol. 37, p. 4201.
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Azev, Y.A., Koptyaeva, O.S., Eltsov, O.S. et al. Indole-3-carbaldehydes Arylhydrazones as Multisite C-Nucleophiles in the Reactions with Quinazoline. Russ J Gen Chem 90, 1601–1610 (2020). https://doi.org/10.1134/S1070363220090030
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DOI: https://doi.org/10.1134/S1070363220090030