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A. SIDDEKHA, S. H. S. AZZAM, AND M. A. PASHA
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( C-CN), 59.5 (CH2-CO), 56.4 (OCH3), 50.9 (CH2-C C), 35.8 (CH), 32.6 (C<),
29.4 (CH3), 27.5 (CH3). Anal. calcd. for C19H21N3O3(%): C, 67.24; H, 6.24; N,
12.38. Found: C, 67.24; H, 6.24; N, 12.39.
Compound 5d. Mp 305–306 ꢀC; IR (ATR-neat): n 3434, 3323, 3204, 2956,
1
2184, 1661, 1524, 1413, 1347, 1145, 1034, 903 cmꢁ1; H NMR (400 MHz, DMSO-
d6): d 0.95 (s, 3H, Me), 1.04 (s, 3H, Me), 2.09 (d, 2H, J ¼ 16 Hz, CH2) 2.24 (d,
2H, J ¼ 16 Hz, CH2), 3.33 (s, 2H, NH2), 4.41 (s, 1H, CH), 7.19–7.67 (m, 2H, Ph),
7.96–8.09 (m, 2H, Ph), 8.40 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6): d
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196.7 (C O), 164.0 ( C-NH2), 159.5 (C C-NH), 147.1, 146.1, 136.7, 120.6, 120.2,
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116.2 (all ArCs), 120.3 (C-CN), 112.6 (C C-CO), 64.5 ( C-CN), 58.0 (CH2-CO),
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50.8 (CH2-C C), 36.3 (CH), 32.7 (C<), 29.2 (CH3), 27.6 (CH3). Anal. calcd. for
C18H18N4O3(%): C, 63.89; H, 5.36; N, 16.56. Found: C, 63.90; H, 5.36; N, 16.57.
Compound 5e. Mp 269–271 ꢀC; IR (ATR-neat): n 3427, 3322, 3198, 2956,
1
2191, 1662, 1530, 1420, 1375, 1204 cmꢁ1; H NMR (400 MHz, DMSO-d6): d 0.97
(s, 3H, Me), 1.05 (s, 3H, Me), 2.09 (d, 2H, J ¼ 16Hz, CH2), 2.23 (d, 2H, J ¼ 16Hz,
13
CH2), 3.28 (s, 2H, NH2), 4.07 (s, 1H, CH), 5.20 (s, 1H,OH), 6.50–6.92 (m, 3H,
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Ph), 8.93 (s, 1H, NH); C NMR (100 MHz, DMSO-d6): d 197.7 (C O), 163.9
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( C-NH2), 150.1 (C C-NH), 158.4, 147.1, 129.3, 124.5, 120.2, 115.2 (all ArCs),
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112.2 (C-CN), 105.2 (C C-CO), 64.9 ( C-CN), 57.8 (CH2-CO), 50.5 (CH2-C C),
37.1 (CH), 32.7 (C<), 29.1 (CH3), 27.8 (CH3). Anal. calcd. for C18H18N3O2(%): C,
69.88; H, 6.19; N, 13.58. Found: C, 69.89; H, 6.18; N, 13.57.
Compound 5f. Mp 260–262 ꢀC; IR (ATR-neat): n 3408, 3316, 3178, 2930,
2184, 1664, 1629, 1524, 1347, 1216, 1138, 1027, 857, 733 cmꢁ1
;
1H NMR
(400 MHz, DMSO-d6): d 0.95 (s, 3H, Me), 1.03 (s, 3H, Me), 2.08 (d, 2H, J ¼ 16 Hz,
CH2), 2.24 (d, 2H, J ¼ 16 Hz, CH2), 2.53 (s, 2H, NH2), 4.36 (s, 1H, CH), 7.19 (m,
2H, Ph), 7.43 (m, 2H, Ph), 8.18 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6): d
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196.6 (C O), 164.0 ( C-NH2), 159.4 (C C-NH), 153.2, 147.1, 129.5, 124.5 (all
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ArCs), 120.2 (C-CN), 112.6 (C C-CO), 65.7 ( C-CN), 57.8 (CH2-CO), 50.7 (CH2-
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C C), 36.5 (CH), 32.7 (C<), 29.1 (CH3), 27.8 (CH3). Anal. calcd. for
C18H18N4O3(%): C, 63.89; H, 5.36; N, 16.56. Found: C, 63.90; H, 5.36; N, 16.57.
Compound 5g. Mp 270–274 ꢀC; IR (ATR-neat): n 3401, 3302, 3178, 2930,
1
2190, 1668, 1641, 1589, 1498, 1360, 1125 cmꢁ1; H NMR (400 MHz, DMSO-d6): d
1.02 (s, 3H, Me), 1.05 (s, 3H, Me), 2.12 (d, 2H, J ¼ 16 Hz, CH2), 2.64 (d, 2H,
J ¼ 16 Hz, CH2), 3.04 (s, 2H, NH2), 3.35 (s, 3H, OCH3), 3.71 (s, 6H, OCH3), 4.13
(s, 1H, CH), 6.37 (m, 2H, Ph), 8.89 (s, 1H, NH); 13C NMR (100 MHz, DMSO-
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=
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d6): d 196.6 (C O), 163.7 ( C-NH2), 159.2 (C C-NH), 153.6, 141.3, 137.0, 120.6
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(all ArCs), 113.2 (C-CN), 105.0 (C¼C-CO), 60.8 ( C-CN), 59.2 (CH2-CO), 56.6
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(OCH3), 50.8 (CH2-C C), 36.5 (CH), 32.6 (C<), 29.5 (CH3), 27.4 (CH3). Anal.
calcd. for C18H18N3O4(%): C, 65.78; H, 6.57; N, 10.96. Found: C, 65.78; H, 6.57;
N, 10.50.
SUPPORTING INFORMATION
Full experimental detail, IR, CHN analysis, and 1H and 13C NMR spectra can
be found via the Supplementary Content section of this article’s Web page.