A new and facile synthesis of N-Benzyl-N’-acylureas via reaction of dibenzoylhydrazine carboxamide and benzylamines

Downloads

[1] Solinas, A.; Faure, H.; Roudaut, H.; Traiffort, E.; Schoenfelder, A.; Mann, A.; Manetti, F.; Taddei, M.; Ruat, M. Acylthiourea, Acylurea, and Acylguanidine Derivatives with Potent Hedgehog Inhibiting Activity. J. Med. Chem. 2012, 55, 1559–1571. DOI: 10.1021/jm2013369. [2] Klabunde, T.; Wendt, K. U.; Kadereit, D.; Brachvogel, V.; Burger, H.-J.; Herling, A. W.; Oikonomakos, N. G.; Kosmopoulou, M. N.; Schmoll, D.; Sarrubi, E.; von Roedern, E.; Schönafinger, K.; Defossa, E. Acyl Ureas as Human Liver Glycogen Phosphorylase Inhibitors for the Treatment of Type 2 Diabetes. J. Med. Chem. 2005, 48, 6178–6193. DOI: 10.1021/jm049034y. [3] Librowski, T.; Kubacka, M.; Meusel, M.; Scolari, S.; Müller, C. E.; Gütschow, M. Evaluation of Anticonvulsant and Analgesic Effects of Benzyl- and Benzhydryl Ureides. Eur. J. Pharmacol. 2007, 559, 138–149. DOI: 10.1016/j.ejphar.2006.12.002. [4] Wang, H.; Lim, Z.-Y.; Zhou, Y.; Ng, M.; Lu, T.; Lee, K.; Sangthonpitag, K.; Goh, K.G.; Wang, X.; Wu, X.; Khng, H. H.; Goh, S. K.; Ong, W. C.; Bonday, Z.; Sun, E. T. Acylurea Connected Straight Chain Hydroxamates as Novel Histone Deacetylase Inhibitors: Synthesis, SAR, and In Vivo Antitumor Activity. Bioorg. Med. Chem. Lett. 2010, 20, 3314–3321. DOI: 10.1016/j.bmcl.2010.04.041 [5] Wiley, P. F. The reaction of amides with isocyanates. J. Am. Chem. Soc. 1949, 71, 1310–1311. DOI: 10.1021/ja01172a047. [6] Abbasi, S.; Miraki, M.K.; Radfar, I.; Karimi, M.; Heydari, A. Efficient Synthesis of N-Acylureas Using Copper Oxide Supported on Magnetic Nanoparticles in Deep Eutectic Solvent. ChemistrySelect 2018, 3, 77–80. DOI: 10.1002/slct.201702315. [7] Stokes, S.; Martin, N. A Simple and Efficient Synthesis of N-benzoyl Ureas. Tetrahedron Lett. 2012, 53, 4802–4804. DOI: 10.1016/j.tetlet.2012.05.158. [8] Häcker, H.-G.; Meusel, M.; Aschfalk, M.; Gütschow, M. Solid-Phase Synthesis of Disubstituted N-Acylureas from Resin-Bound Ureas and Acyl Chlorides. ACS Comb. Sci. 2011, 13, 59–64. DOI: 10.1021/co100020b. [9] Il’in, M. V.; Lesnikova, L.A.; Bolotin, D.S.; Novikov, A.S.; Suslonov, V. V.; Kukushkin, V. Y. A One-pot Route to N-acyl Ureas: a Formal Four-component Hydrolytic Reaction Involving Aminonitrones and Isocyanide Dibromides. New J. Chem. 2020, 44, 1253–1262. DOI: 10.1039/C9NJ05445F. [10] Shi, D. H.; Harjani, J.R.; Gable, R. W.; Baell, J. B. Synthesis of 3-(Alkylamino)-, 3-(Alkoxy)-, 3-(Aryloxy)-, 3-(Alkylthio)-, and 3-(Arylthio)-1,2,4-triazines by Using a Unified Route with 3-(Methylsulfonyl)-1,2,4-triazine. Eur. J. Org. Chem. 2016, 16, 2842–2850. DOI: 10.1002/ejoc.201600267. [11] Irannejad, H.; Naderi, N.; Emami, S.; Ghadikolaei, R. Q.; Foroumadi, A.; Zafari, T.; Mazar-Atabaki, A.; Dadshpour, S. Microwave-assisted Synthesis and Anticonvulsant Activity of 5,6-Bisaryl-1,2,4-triazine-3-thiolderivatives. Med. Chem. Res. 2014, 23, 2503–2514. DOI: 10.1007/s00044-013-0843-6. [12] Tuylu Kucukkilinc T.; Safari Yanghagh K.; Ayazgok, B.; Ali Roknipour, M.; Homayouni Moghadam, F.; Moradi, A.; Emami, S.; Amini, M.; Irannejad, H. Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H2O2 and Aβ-induced neurotoxicity. Med. Chem. Res. 2017, 26, 3057–3071. DOI: 10.1007/s00044-017-2003-x.