1302
M. A. N. Mosselhi
7-Amino-3-phenylcarbamoyl-1-0p-methylphenyl)-[1,2,4]triazolo[4,3-a]pyrimidin-
501H)-one ꢀ8g; C19H16N6O2)
1
Yield: 82%; m.p.: 225ꢀC; IR: ꢂ 3485, 3320, 1690, 1650cmÀ 1; H NMR ꢀDMSO-d6, ꢃ, 250MHz):
2.30 ꢀs, CH3), 5.00 ꢀs, CH), 7.10 ꢀs, NH2), 7.3±8.0 ꢀm, 9 Ar±H), 11.80 ꢀs, NH) ppm; MS: m=z
ꢀ%) 360 ꢀM , 100), 220 ꢀ50), 180 ꢀ40), 149 ꢀ11), 91 ꢀ100), 77 ꢀ63).
Reaction of 8 with methyl 0Z)-2-benzoylamino-3-dimethylamino propenoate 11;
general procedure
To a boiling solution of 0.01mol of compound 8 in 50cm3 glacial acetic acid, 0.01mol of methyl ꢀZ)-
2-benzoylamino-3-dimethylamino propenoate ꢀ11) were added, and the mixture was re¯uxed for
6±10 h ꢀTLC monitoring). The solvent was evaporated in vacuo, and the residue was recrystallized
from dioxane:ethanol 1:1 to give 12.
Methyl 0Z)-2-benzoylamino-3-01,3-diphenyl[1,2,4]triazolo[4,3-a]pyrimidin-7-yl)-amino
propenoate ꢀ12a; C28H22N6O4)
Yield: 86%; m.p.: 180±182ꢀC; IR: ꢂ 3435, 1710, 1680, 1660cmÀ 1
;
1H NMR ꢀDMSO-d6, ꢃ,
250 MHz): 3.71 ꢀs, COOCH3), 6.10 ꢀs, 60-CH) 7.3±8.20 ꢀm, 15 Ar±H), 8.85 ꢀd, J 12 Hz, 3-CH),
9.60 ꢀs, NH), 10.20 ꢀd, J 12 Hz, 3-NH) ppm; 13C NMR ꢀDMSO-d6, ꢃ, 62.9MHz): 51, 68, 83, 107,
121, 121, 124, 127, 128, 129, 130, 132, 133, 134, 136, 138, 139, 147, 152, 157, 162, 165 ppm; MS:
m=z 506 ꢀM , 80), 475 ꢀ25), 385 ꢀ25), 265 ꢀ10), 105 ꢀ100), 91 ꢀ50), 77 ꢀ75).
Methyl 0Z)-2-benzoylamino-3-03-acetyl-1-phenyl[1,2,4]triazolo[4,3-a]pyrimidin-7-yl)-amino
propenoate ꢀ12b; C28H22N6O4)
1
Yield: 75%; m.p.: 232±234ꢀC; IR: ꢂ 3455, 1725, 1700, 1675, 1660 cmÀ 1; H NMR ꢀDMSO-d6, ꢃ,
250 MHz): 2.70 ꢀs, COCH3), 3.80 ꢀs, COOCH3), 6.00 ꢀs, 60-CH), 7.2±8.10 ꢀm, 10 Ar±H), 8.50 ꢀd,
J 12, 3-CH), 9.10 ꢀs, 1H, NH), 10.30 ꢀd, J 12 Hz, 3-NH) ppm; MS: m=z 472 ꢀM , 65), 440 ꢀ20),
384 ꢀ20), 265 ꢀ5), 105 ꢀ100), 91 ꢀ40), 77 ꢀ70).
Methyl 0Z)-2-benzoylamino-3-03-ethoxycarbonyl-1-phenyl[1,2,4]triazolo[4,3-a]pyrimidin-7-yl)-
amino propenoate ꢀ12c; C25H22N6O6)
1
Yield: 68%; m.p.: 191±192ꢀC; IR: ꢂ 3430, 1750, 1710, 1675, 1655cmÀ 1; H NMR ꢀDMSO-d6, ꢃ,
250 MHz): 1.39 ꢀt, J 7.1 Hz, CH3), 3.72 ꢀs, 3H, H), COOCH3), 4.5 ꢀq, J 7.1 Hz, CH2), 5.99 ꢀs,
60-CH) 7.30±8.10 ꢀm, 5 Ar±H), 8.50 ꢀd, J 12Hz, 3-CH), 8.80 ꢀs, NH), 9.25 ꢀd, J 12Hz, 3-NH),
10.50 ꢀs, NH) ppm; MS: m=z 502 ꢀM , 80), 470 ꢀ25), 385 ꢀ20), 265 ꢀ10), 105 ꢀ90), 91 ꢀ50),
77 ꢀ100).
Methyl 0Z)-2-benzoylamino-3-03-phenylcarbamoyl-1-phenyl[1,2,4]
triazolo[4,3-a]pyrimidin-7-yl)-amino propenoate ꢀ12d; C29H23N7O5)
Yield: 76%; m.p.: 250±251ꢀC; IR: ꢂ 3448, 1708, 1660, 1638cmÀ 1
;
1H NMR ꢀDMSO-d6, ꢃ,
250 MHz): 3.72 ꢀs, COOCH3), 5.68 ꢀs, 60-CH) 7.15±8.18 ꢀm, 15 Ar±H), 8.40 ꢀd, J 12Hz, 3-CH),
8.77 ꢀs, NH), 9.30 ꢀd, 12Hz, 3-NH), 12.10 ꢀs, 1H, NH) ppm; 13C NMR ꢀDMSO-d6, ꢃ, 62.9MHz): 52,
67, 83, 107, 120, 122, 125, 128.2, 128.5, 129, 130, 132, 133, 134, 136, 138, 139, 148, 153, 157, 159,
165, 166 ppm; MS: m=z 549 ꢀM , 50), 517 ꢀ20), 384 ꢀ20), 265 ꢀ15), 237 ꢀ15), 119 ꢀ100), 91 ꢀ80),
77 ꢀ20).