Abstract
4-Substituted O-benzyl benzamide oximes reacted with 2-iodobenzonitrile in the presence of 0.1 mol % of [Pd2(dba)3], 0.2 mol % of XantPhos, and 1.5 equiv of Cs2CO3 in dioxane under argon to give 2-arylquinazolin-4-amines. The described reaction is a new type of cascade processes, which affords 4-amino-quinazoline derivatives without using highly reactive chlorinating agents.
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Lipunova, G.N., Nosova, E.V., Charushin, V.N., and Chupakhin, O.N., Russ. Chem. Rev., 2016, vol. 85, no. 7, p. 759. doi https://doi.org/10.1070/rcr4591
Mphahlele, M.J., Maluleka, M.M., Aro, A., McGaw, L.J., and Choong, Y.S., J. Enzyme Inhib. Med. Chem., 2018, vol. 33, no. 1, p. 1516. doi https://doi.org/10.1080/14756366.2018.1510919
Liu, F., Huai, Z., Xia, G., Song, L., Li, S., Xu, Y., Hong, K., Yao, M., Liu, G., and Huang, Y., Bioorg. Med. Chem. Lett., 2018, vol. 28, no. 14, p. 2561. doi https://doi.org/10.1016/j.bmcl.2018.05.033
Fan, Y.H., Ding, H.W., Liu, D.D., Song, H.R., Xu, Y.N., and Wang, J., Bioorg. Med. Chem., 2018, vol. 26, no. 8, p. 1675. doi https://doi.org/10.1016/j.bmc.2018.02.015
Hao, C., Zhao, F., Song, H., Guo, J., Li, X., Jiang, X., Huan, R., Song, S., Zhang, Q., Wang, R., Wang, K., Pang, Y., Liu, T., Lu, T., Huang, W., Wang, J., Lin, B., He, Z., Li, H., Li, F., Zhao, D., and Cheng, M., J. Med. Chem., 2018, vol. 61, no. 1, p. 265. doi https://doi.org/10.1021/acs.jmedchem.7b01342
Feng, J.B. and Wu, X.F., Org. Biomol. Chem., 2015, vol. 13, no. 43, p. 10656. doi https://doi.org/10.1039/c5ob01587a
Yan, S., Dong, Y., Peng, Q., Fan, Y., Zhang, J., and Lin, J.-B., RSC Adv., 2013, vol. 3,5563. doi https://doi.org/10.1039/c3ra23059g
Qiao, R., Fu, H., Yang, X., Liu, H., Jiang, Y., and Zhao, Y., Synlett, 2010, vol. 2010,101. doi https://doi.org/10.1055/s-0029-1218530
Chen, D., Yang, L., Luo, H., Sun, Y., Shi, Z., Ni, K., and Li, F., Synthesis, 2017, vol. 49, no. 11, p. 2535. doi https://doi.org/10.1055/s-0036-1588727
Jia, F.C., Zhou, Z.W., Xu, C., Cai, Q., Li, D.K., and Wu, A.X., Org. Lett., 2015, vol. 17, no. 17, p. 4236. doi https://doi.org/10.1021/acs.orglett.5b02020
Bolotin, D.S., Bokach, N.A., Demakova, M.Ya., and Kukushkin, V.Yu., Chem. Rev., 2017, vol. 117, no. 21, p. 13039. doi https://doi.org/10.1021/acs.chemrev.7b00264
Patil, S.S., Mhaske, P.C., Patil, S.V., and Bobade, V.D., J. Heterocycl. Chem., 2011, vol. 48, no. 3, p. 652. doi https://doi.org/10.1002/jhet.572
Bolotin, D.S., Bokach, N.A., and Kukushkin, V.Yu., Coord. Chem. Rev., 2016, vol. 313,62. doi https://doi.org/10.1016/j.ccr.2015.10.005
Dondoni, A., J. Chem. Soc., Chem. Commun., 1975, no. 18, p. 761. doi https://doi.org/10.1039/C39750000761
Akazome, M., Kondo, T., and Watanabe, Y., J. Mol. Catal., 1993, vol. 80, no. 3, p. 383. doi https://doi.org/10.1016/0304-5102(93)85011-H
Mahajan, U.S., Godinde, R.R., and Mandhare, P.N., Synth. Commun., 2011, vol. 41,2195. doi https://doi.org/10.1080/00397911.2010.488307
Duros, V., Sartzi, H., Teat, S.J., Sanakis, Y., Roubeau, O., and Perlepes, S.P., Inorg. Chem. Commun., 2014, vol. 50,117. doi https://doi.org/10.1016/j.inoche.2014.10.017
Anbazhagan, M., Stephens, C.E., and Boykin, D.W., Tetrahedron Lett., 2002, vol. 43, no. 23, p. 4221. doi https://doi.org/10.1016/S0040-4039(02)00775-X
Abele, E., Rubina, K., Golomba, L., and Abele, R., Heterocycl. Lett., 2012, vol. 2, no. 1, p. 85.
Xu, M.M., Cao, W.B., Xu, X.P., and Ji, S.J., Chem. Commun., 2018, vol. 54, no. 89, p. 12602. doi https://doi.org/10.1039/c8cc07721e
Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans., 1987, vol. 12, p. S1. doi https://doi.org/10.1039/P298700000S1
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64,112. doi https://doi.org/10.1107/S0108767307043930
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, no. 2, p. 339. doi https://doi.org/10.1107/S0021889808042726
CrysAlisPro. Data Collection and Processing Software for Agilent X-ray Diffractometers. 1.171.36.20, Agilent Technologies. 2012.
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Demakova, M.Y., Islamova, R.M. & Suslonov, V.V. Palladium-Catalyzed Synthesis of 4-Aminoquinazolines from Amide Oxime Ethers and 2-Iodobenzonitrile. Russ J Gen Chem 89, 668–672 (2019). https://doi.org/10.1134/S1070363219040054
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DOI: https://doi.org/10.1134/S1070363219040054