J. C. Rodrı´guez-Domı´nguez et al. / Tetrahedron Letters 48 (2007) 5777–5780
5779
29. Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1999,
319–320.
Acknowledgements
30. Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1999,
321–323.
31. Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Babu, T. R.;
Reddy, V. V. N. Tetrahedron Lett. 2002, 43, 2657–2659.
32. Shirini, F.; Zolfigol, M. A.; Mollarazi, E. Synth. Commun.
2006, 36, 2307–2310.
´
We want to thank the Conseil Regional de Lorraine,
´
France, for supporting this work and Mrs. Veronique
Poddig for recording the NMR spectrum. We are grate-
ful to the referees for comments and suggestions.
33. General procedure when ZrCl4 is used: Urea or thiourea
(1.3 mmol) was added to a mixture of a,b-dicarbonyl
compound (1 mmol) (or cyclic ketone, see entry X in Table
1) and aldehyde (1 mmol), left at 90–100°C; then ZrCl4
(5% mol) was added and left with good stirring at the same
temperature for the referred time (see Table 1). To the
obtained solid was added ethanol (see Table 1) and left to
stir at room temperature until the mixture becomes
homogeneous. Water is slowly added (see Table 1) and
left to stir at room temperature for 1 h. The precipitate
was filtered and washed with a similar quantity of a
mixture of ethanol/water (see Table 1) and dried at 60 °C
until constant weight.
References and notes
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1-[4-(2-Chloro-5-nitrophenyl)-6-methyl-2-thioxo-1,2,3,4-
tetrahydro-5-pyrimidinyl]ethanone (2): 1H NMR (DMSO-
d6): d 10.48 (s, 1H, NH); 9.78 (s, 1H, NH); 8.11 (dd, 1H,
H-Ph); 7.95 (d, J = 2.52 Hz, 1H, H-Ph); 7.74 (d,
J = 8.85 Hz, 1H, H-Ph); 5.71 (d, J = 3.30 Hz, 1H, H-4);
2.39 (s, 3H, CH3); 2.17 (s, 3H, CH3). 13C NMR (DMSO-
d6): d 194.32, 174.09, 146.70, 145.44, 141.67, 138.85,
131.30, 124.17, 123.62, 109.67, 51.86, 30.67, 18.28. Elem.
Anal. Calcd: C, 47.93; H, 3.71; Cl, 10.88; N, 12.90; O,
14.73; S, 9.84. Found: C, 47.88; H, 3.65; Cl, 10.93; N,
12.95; O, 14.80; S, 9.79.
1-[4-(3-Chlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-
5-pyrimidinyl]ethanone (3): 1H NMR (DMSO-d6): d 10.36
(s, 1H, NH); 9.79 (s, 1H, NH); 7.43–7.37 (m, 2H, H-Ph);
7.24 (d, J = 1.7 Hz, H, H-Ph); 7.18–7.14 (m, 2H, H-Ph);
5.28 (d, J = 3.85 Hz, H-4); 2.42 (s, 3H, CH3); 2.23 (s, 3H,
CH3). 13C NMR (DMSO-d6): d 194.63, 174.30, 145.19,
145.14, 133.13, 130.59, 127.61, 126.35, 125.04, 110.20,
53.06, 30.55, 18.31. Elem. Anal. Calcd: C, 55.61; H, 4.67;
Cl, 12.63; N, 9.98; O, 5.70; S, 11.42. Found: C, 55.70; H,
4.73; Cl, 12.60; N, 10.01; O, 5.56; S, 11.40.
1-[6-Methyl-4-(2-naphthyl)-2-thioxo-1,2,3,4-tetrahydro-5-
pyrimidinyl]ethanone (4): 1H NMR (DMSO-d6): d 10.36
(s, 1H); 9.89 (s, 1H, NH); 7.94–7.88 (m, 3H, H-Ph); 7.75 (s,
1H, H-Ph); 7.53–7.44 (m, 3H, H-Ph); 5.49 (d, J = 3.25 Hz,
1H); 2.40 (s, 3H); 2.20 (s, 3H). 13C NMR (DMSO-d6): d
194.81, 174.07, 144.72, 140.19, 132.41, 132.23, 128.55,
127.89, 127.45, 126.35, 126.13, 124.98, 124.91, 110.18,
54.03, 30.39, 18.29. Elem. Anal. Calcd: C, 68.89; H, 5.44;
N, 9.45; O, 5.40; S, 10.82. Found: C, 68.92; H, 5.40; N,
9.48; O, 5.35; S, 10.85.
6. (a) Abelman, M. M.; Smith, S. C.; James, D. R.
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34. General procedure when ZrOCl2Æ8H2O is used: Reactions
were carried out in the same way as for ZrCl4. In this case
10 mol % of ZrOCl2Æ8H2O was used. Quantities of etha-
nol/water mixtures are referred in Table 2.
21. Sabitha, G.; Reddy, G. S. K. K.; Reddy, Ch. S.; Yadav, J.
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1-[4-(2-Chlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-
5-pyrimidinyl]ethanone (18): 1H NMR (DMSO-d6): d
10.36 (s, 1H, NH); 9.65 (d, J = 2.5 Hz, 1H, NH); 7.48–
7.44 (m, 1H, H-Ph); 7.35–7.31 (m, 2H, H-Ph); 7.27–7.26
(m, 1H, H-Ph); 5.70 (d, J = 5 Hz, 1H, H-4); 2.38 (s, 3H,
CH3); 2.12 (s, 3H, CH3). 13C NMR (DMSO-d6): d 194.53,
173.88, 144.86, 139.69, 131.83, 129.86, 129.06, 127.89,
109.68, 51.55, 30.25, 18.15. Elem. Anal. Calcd: C, 55.61;
H, 4.67; Cl, 12.63; N, 9.98; O, 5.70; S, 11.42. Found: C,
55.64; H, 4.70; Cl, 12.60; N, 10.02; O, 5.59; S, 11.45.
Ethyl 4-(2-chloro-5-nitrophenyl)-6-phenyl-2-thioxo-1,2,
3,4-tetrahydro-5-pyrimidinecarboxylate (22): 1H NMR
(DMSO-d6): d 10.74 (s, 1H, NH), 9.83 (d, J = 1.75 Hz,
´
´
25. Rodrıguez-Domınguez, J. C.; Kirsch, G. Synthesis 2006,
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