1556
HETEROCYCLES, Vol. 68, No. 8, 2006
6517; I. Saxena, D. C. Borah, and J. C. Sarma, Tetrahedron Lett., 2005, 46, 1159; U. K. Nadir and A.
Singh, Tetrahedron Lett., 2005, 46, 2083; D. Guzmán-Lucero, J. Guzmán, D. Likhatchev, and R.
Martinez-Palou, Tetrahedron Lett., 2005, 46, 1119.
19. A. R. Khosropour, M. M. Khodaei, and K. Ghozati, Chem. Lett., 2004, 33, 1378; M. M. Khodaei, A.
R. Khosropour, and M. Kookhazadeh, Tetrahedron Lett., 2004, 45, 1725; M. M. Khodaei, A. R.
Khosropour, and M. Kookhazadeh, Synlett, 2004, 1980; M. M. Khodaei, A. R. Khosropour, and M.
Kookhazadeh, Can. J. Chem., 2005, 83, 209; M. M. Khodaei, A. R. Khosropour, and P. Fattahpour,
Tetrahedron Lett., 2005, 46, 2105; A. R. Khosropour, M. M. Khodaei, and H. Moghannian, Synlett,
2005, 955; A. R. Khosropour, M. M. Khodaei, M. Beygzadeh, and M. Jokar, Heterocycles, 2005, 65,
767.
20. I. Mohammadpoor-Baltork, H. Aliyan, and A. R. Khosropour, Tetrahedron, 2001, 57, 5851; I.
Mohammadpoor-Baltork and A. R. Khosropour, Monatsh. Chem., 2002, 133, 189; A. R. Khosropour,
M. M. Khodaei, and K. Ghozati, Tetrahedron Lett., 2004, 45, 3525; A. R. Khosropour, M. M.
Khodaei, and K. Ghozati, Russian J. Org. Chem., 2004, 1332; A. R. Khosropour, M. M. Khodaei,
and K. Ghozati, Z. Naturforsch. B, 2005, 512; M. M. Khodaei, A. R. Khosropour, and K. Ghozati, J.
Braz. Chem. Soc., 2005, 16, 673.
21. A. R. Khosropour, M. M. Khodaei, and K. Ghozati, Chem. Lett., 2004, 33, 304.
22. S. B. Cunha, R. Lima, and A. R. Souza, Tetrahedron Lett., 2002, 43, 49; E. M. Keramane, B. Boyer,
and J. P. Roque, Tetrahedron, 2001, 57, 1909; E. M. Keramane, B. Boyer, and J. P. Roque,
Tetrahedron Lett., 2001, 42, 855.
23. G. Wilkinson, R. D. Gillard, and J. A. McCleverty, ‘Comprehensive Coordination Chemistry,’ Vol.
3, Pergamon Press, London, 1987, p. 292.
24. N. Srivastava and B. K. Banik, J. Org. Chem., 2003, 68, 2109; K. J. Eash, M. S. Pulia, L. C. Wieland,
and R. S. Mohan, J. Org. Chem., 2000, 65, 8399; H. Suzuki, T. Ikegami, and Y. Matano, Synthesis,
1997, 249; J. A. Marshall, Chemtracts, 1997, 1064; J. Reglinski, ‘Chemistry of Arsenic, Antimony
and Bismuth’ ed. by N. C. Norman, Blackie Academic and Professional, New York, 1998, p. 403.
25. Typical Procedure for the Synthesis of 4-(4-Chlorophenyl)-6-(4-methoxyphenyl)-1H-pyrimidin-2-one
promoted by Bi(OTf)3-TCT(Table 1, Entry 12): 4-Chlorobenzaldehyde (1d) (140.6 mg, 1 mmol),
4-methoxyacetophenone (2d) (150 mg, 1 mmol), urea (90 mg, 1.5 mmol), TCT (184 mg, 1 mmol)
and Bi(OTf)3 (7 mg, 0.01 mmol) were taken into a reaction tube and thoroughly mixed with a glass
rod. The resulting mixture was placed in the microwave cavity and irradiated for 15 min at 300 w.
After completion of the reaction, as indicated by TLC, the mixture was allowed to cool. The
precipitate was washed with cooled ethanol (10 ml) and recrystallized by ethyl acetate to give
pyrimidinone (3f) in 91% yield. mp 287-290 °C. IR (KBr) 3429, 3100, 2890, 1617, 1582, 810, 600