Book of Abstracts - Ruhr-Universität Bochum

P-22
ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum
Green Chemistry in the Production of Ferrocene Derivatives Using Recyclable
Solid Heteropolyacids as Catalysis
Jorge Jios, a Gustavo Romanelli, b and Nils Metzler-Nolte *c
a Laseisic (CIC-CONICET-UNLP), Departamento de Química, Facultad de Ciencias Exactas, UNLP.
Camino Centenario e/505 y 508, CP1897, Gonnet, Argentina. b Centro de Investigación y Desarrollo
en Ciencias Aplicadas “Dr. J. J. Ronco” (CINDECA), Departamento de Química, Facultad de
Ciencias Exactas, UNLP-CONICET. Calle 47 Nº 257, B1900AJK La Plata, Argentina. c Lehrstuhl für
Anorganische Chemie I, Bioanorganische Chemie, Fakultät für Chemie und Biochemie, Ruhr-
Universität Bochum, Universitätsstrasse150, D-44801 Bochum, Germany. E-mail:
jljios@quimica.unlp.edu.ar
Dihydropyrimidinone are known to exhibit a wide range of biological activities such as antiviral,
antitumour, antibacterial, and anti-inflammatory properties. 1 Several reagents/methods have been
reported for their preparation under milder and more efficient procedures such as Amberlyst-15,
Nafion-H, KSF clay with dry acetic acid under microwave irradiation, ionic liquids, cerric ammonium
nitrate under ultrasonication, Lewis acids with transition metals, lanthanides, and indium chloride. 2 In
this work we present an improved procedure for the obtention of dihydropyrimidinones bearing
ferrocene in a three component one-pot condensation reaction using heteropolyacid catalysts (Figure
1).
R
Fe +2
+
O O
C
O
H
R´
NH 2CONH 2
Superacid Catalyst
The results are discussed in terms of the catalyst used, their selectivity and the reaction conversion
degree. The aim of this work is investigate a convenient synthesis for the production of new
metallocene carrying heterocyclic compounds with biological activities. The spectral data are
discussed in detail.
References
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(b) J. Peng, Y. Deng, Tetrahedron Lett. 2001, 42, 5917-5919. (c) J. S. Yadav, B. V. S. Reddy, K. B.
Reddy, K. S. Raj, A. R. J. Prasad, Chem. Soc. Perkin Trans. 1 2001, 1939-1941. (d) E. H. Hu, D. R.
Sidler, U. H. Dolling, J. Org. Chem. 1998, 63, 3454-3457. (e) Y. Ma, C. Qian, L. Wang, M. Yang, J.
Org. Chem. 2000, 65, 3864-3868. (f) J. Lu, Y. Bai, Z. Wang, B. Yang, H. Ma, Tetrahedron Lett. 2000,
41, 9075-9078. (g) B. C. Rannu, A. Hajra, U. Jana, J. Org. Chem. 2000, 65, 6270-6272. (h) H. N.
Karade, M. Sathe, M. P. Kaushik. Molecules 2007, 12, 1341-1351.
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R'
O
R
Fe +2
N
H
NH
O