2
626 Akhter et al.
Asian J. Chem.
1
8
1
=
40, 770 (C-H bending of aromatic ring); H NMR δ (in ppm):
0.28 (s, 1H, NH, H-1), 9.75 (s, 1H, NH, H-3), 7.28 (m, 5H, J
the use of costly and environmentally toxic catalyst. As well
as the reaction time is very short. Except production of water
vapour, the reaction is hundred percent atoms economic and
therefore, green in nature.
8.0 Hz, ArH), 5.31 (d, 1H, J = 3.8, H-4), 2.33 (s, 3H, CH -
3
13
CO), 2.15 (s, 3H, CH
3
-C=C); C NMR δ (in ppm): 194.84
(
CH
3
-CO), 174.12 (C-2), 144.59, 142.93, 128.67 (C × 2),
27.75 (C × 2) (6C-aromatic), 126.59 (C-5), 110.52 (C-6),
3.85 (C-4), 30.45 (CH -CO), 18.31 (CH -C=C).
-Aceto-4-(4-chlorophenyl)-6-methyl-2-thio-1,2,3,4-
tetrahydropyridimidine (4f): Yield 86 %; white crystalline
solid; m.p. 227-229 °C; R value: 0.33 (CHCl : EtOAc = 1:1);
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3
-1
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3
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1
1
(
(
8
3
1
C-H bending of aromatic ring); H NMR δ (in ppm): 10.33
s, 1H, NH, H-1), 7.83 (s, 1H, NH, H-3), 7.41 (d, 2H, J =
.2Hz, ArH), 7.25 (d, 2H, J = 8.2 Hz, ArH), 5.29 (d, 1H, J =
-CO), 2.17 (s, 3H, CH
-CO), 174.24 (C-2), 144.95, 141.82,
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10.38 (C-6), 53.09 (C-4), 30.54 (CH -CO), 18.36 (CH -C=C).
-Aceto-4-(2-chlorophenyl)-6-methyl-2-thio-1,2,3,4-
tetrahydropyridimidine (4g): Yield 80 %; white crystalline
solid; m.p. 174-175 °C; R value: 0.33 (CHCl : EtOAc = 1:1);
4
.
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13
.34, H-4), 2.33 (s, 3H, CH
3
3
-C=C); C
NMR δ(in ppm): 194.69 (CH
1
1
3
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3
3
5
6
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5
f
3
-1
IR (KBr, νmax, cm ): 3399 (N-H), 3173 (aromatic C-H stret-
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474 (C=C stretching of phenyl), 1371 (aliphatic C-H bending),
3
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7
.
1
1
1
331 (C=S stretching), 1033 (C-Cl stretching), 781, 759, 612
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1
(
C-H bending of aromatic ring); H NMR δ (in ppm): 8.39 (s,
3751 (1932). (c) P. Wipf and A. Cunningham, Tetrahedron Lett., 36,
1
H, NH, H-1), 7.49 (s, 1H, NH, H-3), 7.40 (d, 1H, J = 9 Hz,
ArH), 7.25 (t, 2H, J = 4.2 Hz, ArH), 7.17 (d, 1H, J = 7.2Hz,
ArH), 5.87 (d, 1H, J = 2.4, H-4), 2.40 (s, 3H, CH -CO), 2.02
-C=C); C NMR δ (in ppm): 195.20 (CH -CO),
74.32 (C-2), 143.69, 137.31, 128.28 (C × 2), 128.44 (C × 2)
6C-aromatic), 132.59 (C-5), 108.78 (C-6), 53.10 (C-4), 29.50
CH -CO), 18.98 (CH -C=C).
7
819 (1995).
9
.
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3
13
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(s, 3H, CH
3
3
1
(
(
1
1
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3
3
1
3. (a) E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454
Conclusion
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1
1
4. Y. Ma, C. Qian, L. Wang and M. Yang, J. Org. Chem., 65, 3864 (2000).
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As per literature survey, there are no earlier reports for
the synthesis of dihydropyrimidinones using acetylacetone in
the presence of zinc chloride catalyst under heptane-toluene
reflux condition. This prompted us to develop a method which
neither involves the use of any high boiling solvent nor involves
(
2000).
1
6. B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000).