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A. S. Shawali, T. A. Farghaly / Tetrahedron 60 (2004) 3051–3057
ArH), 7.25 (d, J¼8 Hz, 2H, ArH), 7.70 (d, J¼8 Hz, 2H,
ArH), 12.89 (s, 1H, NH), 16.15 (s, 1H, NH). nmax (KBr)
3147, 3074, 1685, 1608 cm21. MS m/z (%) 377 (Mþþ1,
15), 376 (Mþ, 63), 375 (100), 226 (15), 213 (12), 198 (11),
136 (19), 122 (22), 119 (54), 107 (16), 91 (53), 84 (11), 77
(12).
Ar-CH3), 2.46 (s, 3H, 6-CH3), 6.27 (s, 1H, 5-CH), 7.10 (d,
J¼8 Hz, 2H, ArH), 7.14–7.31 (m, 4H, ArH), 7.72 (d,
J¼8 Hz, 2H, ArH), 12.73 (s, 1H, NH), 15.93 (s, 1H, NH).
nmax (KBr) 3150, 1685, 1620 cm21. MS m/z (%) 382
(Mþþ1, 12), 381 (Mþ, 43), 379 (100), 226 (13), 217 (12),
136 (51), 119 (30), 91 (48), 84 (22).
3.4.10. 2-[N-2-Di(4-methylphenyl)-2-oxo-ethanehydra-
zonoyl]-6-methyl-4(3H)-pyrimidinone (12b). (3.06 g,
85%) as orange plates, mp 238 8C. (Found: C, 70.2; H,
5.4; N, 15.6. C21H20N4O2 (360.42) requires: C, 69.98; H,
5.59; N, 15.54%). dH (CDCl3) 2.35 (s, 3H, Ar-CH3), 2.40 (s,
3H, 6-CH3), 2.45 (s, 3H, 6-CH3), 6.24 (s, 1H, 5-CH–), 7.10
(d, J¼8 Hz, 2H, ArH), 7.16 (d, J¼8 Hz, 2H, ArH), 7.25 (d,
J¼8 Hz, 2H, ArH), 7.71 (d, J¼8 Hz, 2H, ArH), 12.82 (s, 1H,
3.4.15. 2-[N-(3-Nitrophenyl)-2-oxo-2-(4-methylphenyl)-
ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinone
(12g). (3.13 g, 80%) as orange solid, mp 244 8C. (Found: C,
61.1; H, 4.5; N, 17.6. C20H17N5O4 (391.39) requires: C,
61.38; H, 4.38; N, 17.89%). dH (CDCl3) 2.44 (s, 3H,
ArCH3), 2.48 (s, 3H, 6-CH3), 6.29 (s, 1H, 5-CH), 7.31 (d,
J¼8 Hz, 2H, ArH), 7.73 (d, J¼8 Hz, 2H, ArH), 7.46–7.57
and 7.91–8.06 (m, 4H, ArH), 12.7 (s, 1H, NH), 16.00 (s, 1H,
NH). nmax (KBr) 3425, 3093, 1689, 1620 cm21. MS m/z (%)
392 (Mþþ1, 5), 391 (Mþ, 24), 390 (73), 228 (11), 226 (17),
136 (87), 130 (10), 119 (62), 91 (100), 84 (34).
NH), 16.1 (s, 1H, NH); nmax (KBr) 3143, 1666, 1616 cm21
.
MS m/z (%) 360 (Mþ, 42), 359 (100), 226 (12), 197 (17),
136 (29), 119 (40), 91 (75), 84 (18), 77 (16).
3.4.11. 2-[N-(3-Methylphenyl)-2-oxo-2-(4-methylphenyl)-
ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinone
(12c). (2.63 g, 73%) as orange solid, mp 190 8C. (Found: C,
70.3; H, 5.4; N, 15.6. C21H20N4O2 (360.42) requires: C,
69.98; H, 5.59; N, 15.54%). dH (CDCl3) 2.33 (s, 3H,
Ar-CH3), 2.41 (s, 3H, ArCH3), 2.45 (s, 3H, 6-CH3), 6.24 (s,
1H, 5-CH), 6.98 (d, J¼8 Hz, 2H, ArH), 7.00–7.28 (m, 4H,
ArH), 7.72 (d, J¼8 Hz, 2H, ArH), 12.82 (s, 1H, NH), 15.95
(s, 1H, NH). nmax (KBr) 3170, 1681, 1620 cm21. MS m/z
(%) 360 (Mþ, 40), 359 (100), 226 (10), 197 (13), 136 (24),
119 (27), 91 (56), 84 (14), 77 (10).
3.4.16. 2-[N-(4-Nitrophenyl)-2-oxo-2-(4-methylphenyl)-
ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinone
(12h). (3.13 g, 80%) as yellow solid, mp 296 8C. (Found: C,
60.3; H, 4.1; N, 17.7. C20H17N5O4 (391.39) requires: C,
61.38; H, 4.38; N, 17.89%). dH (CDCl3) 2.44 (s, 3H,
ArCH3), 2.48 (s, 3H, 6-CH3), 6.31 (s, 1H, 5-CH), 7.26 (d,
J¼8 Hz, 2H, ArH), 7.29 (d, J¼8 Hz, 2H, ArH), 7.73 (d,
J¼9 Hz, 2H, ArH), 8.27 (d, J¼9 Hz, 2H, ArH), 12.6 (s, 1H,
NH), 16.05 (s, 1H, NH). nmax (KBr) 3417, 3086, 1689,
1631 cm21. MS m/z (%) 392 (Mþþ1, 7), 391 (Mþ, 35), 390
(100), 362 (11), 226 (16), 136 (52), 119 (36), 91 (55), 84 (16).
3.4.12. 2-[N-Phenyl-2-oxo-2-(4-methylphenyl)ethane-
hydrazonoyl]-6-methyl-4(3H)-pyrimidinone
3.4.17. 2-(N-Phenyl-2-oxo-2-phenylethanehydrazonoyl)-
3,6-dimethyl-4(3H)-pyrimidinone (13d). (2.58 g, 75%) as
yellow solid, mp 195 8C. (Found: C, 69.15; H, 5.1; N, 16.0.
C20H18N4O2 (346.39) requires: C, 69.35; H, 5.24; N,
16.17%). dH (CDCl3) 2.38 (s, 3H, 6-CH3), 3.36 (s, 3H,
N–CH3), 6.38 (s, 1H, 5-CH), 7.1–8.1 (m, 10H, ArH), 11.10
(s, 1H, NH). dC (DMSO-d6) 23.6, 31.5, 112.4, 115.6, 123.8,
128.7, 130.0, 130.6, 132.7, 134.1, 137.9, 143.6, 153.6,
(12d).
(2.79 g, 80%) as orange crystals, mp 260 8C. (Found: C,
69.2; H, 5.5; N, 16.1. C20H18N4O2 (346.39) requires: C,
69.35; H, 5.24; N, 16.17%). dH (CDCl3) 2.41 (s, 3H,
Ar-CH3), 2.46 (s, 3H, 6-CH3), 6.25 (s, 1H, 5-CH), 7.15 (d,
J¼8 Hz, 2H, ArH), 7.2–7.4 (m, 5H, ArH), 7.72 (2H,
J¼8 Hz, ArH), 12.80 (s, 1H, NH), 16.01 (s, 1H, NH). nmax
(KBr) 3150, 3050, 1666, 1608 cm21. MS m/z (%) 346 (Mþ,
40), 345 (100), 226 (12), 183 (13), 136 (27), 119 (24), 92
(10), 91 (47), 84 (18), 77 (24).
162.2, 163.4, 190.0; nmax (KBr) 3440, 1666, 1627 cm21
.
MSm/z(%) 348 (Mþþ1, 0.3), 347 (Mþ, 2), 226 (12), 169 (18),
158 (18), 150 (66), 136 (13), 105 (63), 89 (16), 77 (100).
3.4.13. 2-[N-(4-Chlorophenyl)-2-oxo-2-(4-methylphenyl)-
ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinone
(12e). (2.86 g, 75%) as orange plates, mp 236 8C. (Found: C,
63.2; H, 4.9; N, 14.5. C20H17ClN4O2 (380.84) requires: C,
63.08; H, 4.50; N, 14.71%). dH (CDCl3) 2.40 (s, 3H,
ArCH3), 2.46 (s, 3H, 6-CH3), 6.26 (s, 1H, 5-CH), 7.12 (d,
J¼8 Hz, 2H, ArH), 7.25 (d, J¼7 Hz, 2H, ArH), 7.32 (d,
J¼8 Hz, 2H, ArH), 7.70 (d, J¼7 Hz, 2H, ArH), 12.74 (s, 1H,
NH), 16.01 (s, 1H, NH). dC (DMSO-d6) 21.7, 23.4, 111.9,
117.3, 118.1, 128.9, 129.3, 129.5, 130.1, 130.9, 136.1,
142.1, 142.8, 156.6, 162.8, 193.1; nmax (KBr) 3182, 1666,
1616 cm21. MS m/z (%) 382 (Mþþ1, 3), 381 (Mþ, 10), 380
(10), 379 (28), 136 (36), 119 (72), 99 (11), 91 (100), 89 (16),
84 (34), 76 (11).
3.4.18. 2-[N-Phenyl-2-oxo-2-(4-methylphenyl)ethane-
hydrazonoyl]-3,6-dimethyl-4(3H)-pyrimidinone (14d).
(2.88 g, 80%) as yellow crystals, mp 170 8C. (Found: C,
69.5; H, 5.3; N, 15.6. C21H20N4O2 (360.4) requires: C,
69.98; H, 5.59; N, 15.54%). dH (CDCl3) 2.24 (s, 3H,
Ar-CH3), 2.42 (s, 3H, 6-CH3), 3.27 (s, 3H, N–CH3), 6.38 (s,
1H, 5-CH), 7.2 (d, J¼8 Hz, 2H, ArH), 7.3–7.5 (m, 5H, ArH),
7.91 (d, J¼8 Hz, 2H, ArH), 10.98 (s, 1H, NH). dC (DMSO-d6)
21.8, 23.6, 31.5, 112.4, 115.6, 123.7, 129.3, 130.0, 130.8,
134.2, 135.1, 143.1, 143.7, 153.7, 162.2, 163.4, 189.2. nmax
(KBr) 3417, 1651, 1627 cm21. MS m/z (%) 361 (Mþþ1, 5),
360 (Mþ, 24.7), 359 (52), 240 (20), 183 (34), 158 (13), 150
(100), 119 (77), 106 (40), 91 (91), 77 (40).
3.4.14. 2-[N-(3-Chlorophenyl)-2-oxo-2-(4-methylphenyl)-
ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinone
(12f). (2.67 g, 70%) as orange crystals, mp 246 8C. (Found:
C, 63.2; H, 4.9; N, 14.4. C20H17ClN4O2 (380.84) requires:
C, 63.08; H, 4.50; N, 14.71%). dH (CDCl3) 2.41 (s, 3H,
References and notes
1. (a) Shawali, A. S.; Abdelkader, M. H.; Eltalbawy, F. M. A.
Tetrahedron 2002, 58, 2875–2880. (b) Shawali, A. S.;