Synthesis of ferrocene-containing six-membered cyclic ureas via α-ferrocenyl carbocations

作者: Aleksandra Minić , Dragana Stevanović , Ivan Damljanović , Anka Pejović , Mirjana Vukićević

DOI: 10.1039/C5RA01383F

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摘要: A series of ferrocene-containing six-membered cyclic ureas (1-aryl-4-ferrocenyl-3-phenyltetrahydropyrimidin-2(1H)-ones) was synthesized (in high-to-excellent yields) by reacting the corresponding aminopropanols with phenyl isocyanate and subsequent intramolecular cyclization thus obtained β-hydroxy (prompted acetic acid), via an α-ferrocenyl carbocation.

参考文章(37)
P. Babczinski, M. Blunck, G. Sandmann, K. Shiokawa, K. Yasui, Substituted Tetrahydropyrimidinones: A New Herbicidal Class of Compounds Inducing Chlorosis by Inhibition of Phytoene Desaturation: 2. Structure-Activity Relationships Pesticide Biochemistry and Physiology. ,vol. 52, pp. 45- 59 ,(1995) , 10.1006/PEST.1995.1029
Otto Meth-Cohn, Alan R. Katritzky, Charles W. Rees, Comprehensive organic functional group transformations II Pergamon , Elsevier Science. ,(1995)
Ran Jiang, Xue-Qiang Chu, Xiao-Ping Xu, Bin Wu, Shun-Jun Ji, Direct C–O Bond Activation Mediated by AcOH: A New Metal-Free Way for α-Functionalization of Ferrocene Alcohols Australian Journal of Chemistry. ,vol. 64, pp. 1530- 1537 ,(2011) , 10.1071/CH11167
Ran Jiang, Ying Zhang, Ye-Chen Shen, Xu Zhu, Xiao-Ping Xu, Shun-Jun Ji, Nucleophilic substitution of ferrocenyl alcohols by cerium ammonium nitrate: C–N, C–S, and C–O bonds formation Tetrahedron. ,vol. 66, pp. 4073- 4078 ,(2010) , 10.1016/J.TET.2010.04.015
Masazumi Tamura, Kensuke Noro, Masayoshi Honda, Yoshinao Nakagawa, Keiichi Tomishige, Highly efficient synthesis of cyclic ureas from CO2 and diamines by a pure CeO2 catalyst using a 2-propanol solvent Green Chemistry. ,vol. 15, pp. 1567- 1577 ,(2013) , 10.1039/C3GC40495A
J. H. Saunders, R. J. Slocombe, The Chemistry of the Organic Isocyanates. Chemical Reviews. ,vol. 43, pp. 203- 218 ,(1948) , 10.1021/CR60135A001
George W. Gokel, Ivar K. Ugi, Preparation and resolution of N,N-dimethyl-o-ferrocenylethylamine. An advanced organic experiment Journal of Chemical Education. ,vol. 49, pp. 294- ,(1972) , 10.1021/ED049P294
Jerry L. Adams, Thomas D. Meek, Shau Ming Mong, Randall K. Johnson, Brian W. Metcalf, cis-4-Carboxy-6-(mercaptomethyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one, a potent inhibitor of mammalian dihydroorotase Journal of Medicinal Chemistry. ,vol. 31, pp. 1355- 1359 ,(1988) , 10.1021/JM00402A018
Patrick Y. S. Lam, Yu Ru, Prabhakar K. Jadhav, Paul E. Aldrich, George V. DeLucca, Charles J. Eyermann, Chong-Hwan Chang, George Emmett, Edward R. Holler, Wayne F. Daneker, Liangzhu Li, Pat N. Confalone, Robert J. McHugh, Qi Han, Renhua Li, Jay A. Markwalder, Steven P. Seitz, Thomas R. Sharpe, Lee T. Bacheler, Marlene M. Rayner, Ronald M. Klabe, Linyee Shum, Dean L. Winslow, David M. Kornhauser, David A. Jackson, Susan Erickson-Viitanen, C. Nicholas Hodge, Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas. Journal of Medicinal Chemistry. ,vol. 39, pp. 3514- 3525 ,(1996) , 10.1021/JM9602571