Reactions of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides
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(t, J = 7.9 Hz, 2H, (3, 5-Har)), 7.61 (dt, J = 1.0 Hz, J = 7.8 Hz, 1H, (600-H)), 7.68
(d, J = 8.0 Hz, 2H, (2, 6-Har)), 7.73 (dt, J = 1.0 Hz, J = 7.8 Hz, 1H, (700-H)), 8.02
(dd, J = 1.0 Hz, J = 7.4 Hz, (500-H)), 8.13 (br. s, 1H, (200-H)), 8.30 (d, J = 7.9 Hz,
1H, (800-H)), 11.99 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6), d: 16.61 (300-CH3),
33.12 (C-30), 35.10 (C-40), 50.02 (C-20); 119.44 (C-2, 6), 123.44 (C-200), 124.07
(C-4), 124.12, 125.59 (C-500, C-800), 128.68 (C-3, 5), 129.44 (C-600, C-700), 129.97
(C-4a00), 132.71 (C-600, C-700), 134.53 (C-300), 139.08 (C-8a00), 139.16 (C-1), 171.85
(C-50), 184.21 (C-400). MS m/z (I, %): 374 [M ? H]? (100). Found, %: C 70.95, H
5.32, N 11.47. Calculated, %: C 70.76, H 5.13, N 11.25. C22H19N3O3.
N0-(3-Methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-(3-methylphenyl)-5-
oxopyrrolidine-3-carbohydrazide (6b)
Yield 3.8 g (98.0%), m.p. 262–263 °C (from the mixture of 2-propanol and
1
dimethylformamide (1:1)). IR, m: 1641, 1674 (C=O), 3079, 3110, 3177 (NH). H
NMR (300 MHz, DMSO-d6), d: 2.09 (s, 3H, (300-CH3)), 2.30 (s, 3H, (3-CH3)),
2.79–2.96 (m, 2H, CH2CO), 4.02–4.21 (m, 2H, NCH2), 4.32 (br. s, CH), 6.95 (d,
J = 7.3 Hz, 1H, (4-Har)), 7.24 (t, J = 8.2 Hz, 1H, (5-Har)), 7.49 (d, J = 6.5 Hz,
1H, (6-Har)), 7.49 (s, 1H, (2-Har)), 7.61 (dt, J = 1.2 Hz, J = 7.8 Hz, 1H, (600-H)),
7.72 (dt, J = 1.4 Hz, J = 7.7 Hz, 1H, (700-H)), 8.02 (dd, J = 1.1 Hz, J = 7.8 Hz,
(500-H)), 8.13 (br. s, 1H, 200-H), 8.29 (d, J = 7.5 Hz, 1H, (800-H)), 11.99 (s, 1H, NH).
1H NMR (300 MHz, CDCl3), d: 2.21 (d, J = 1.2 Hz 3H, (300-CH3)), 2.36 (s, 3H,
(3-CH3)), 3.02–3.17 (m, 2H, CH2CO), 4.17–4.42 (m, 3H, NCH2 ? CH), 7.00 (d,
J = 7.0 Hz, 1H, (4-Har)), 7.26 (t, J = 8.2 Hz, 1H, (5-Har)), 7.41 (d, J = 8.2 Hz,
1H, (6-Har)), 7.46 (s, 1H, (2-Har)), 7.59 (dt, J = 1.3 Hz, J = 7.5 Hz, 1H, (600-H)),
7.67 (dt, J = 1.4 Hz, J = 7.5 Hz, 1H, (700-H)), 7.72 (q, J = 1.2 Hz, 1H, (200-H)),
8.17–8.23 (m, 2H, (500, 800-H)), 10.80 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6),
d: 16.61 (300-CH3), 21.17 (3-CH3), 32.58, 33.16 (C-30), 35.10 (C-40), 50.13 (C-20),
116.71 (C-6), 120.04 (C-2), 123.33 (C-200), 124.12 (C-500, C-800), 124.78 (C-4),
125.59 (C-500, C-800), 128.49 (C-5), 129.43 (C-600, C-700), 129.97 (C-4a00), 132.70
(C-600, C-700), 134.53 (C-300), 137.95 (C-3), 139.07 (C-8a00), 139.12 (C-1), 171.71
(C-50), 175.55 (CONH), 184.20 (C-400). 13C NMR (75 MHz, CDCl3), d: 17.33
(300-CH3), 21.61 (3-CH3), 34.05 (C-30), 35.48 (C-40), 50.32 (C-20), 117.28 (C-6),
120.89 (C-2), 121.41 (C-200), 122.96 (C-500, C-800), 125.91 (C-4), 126.68 (C-500,
C-800), 128.80 (C-5), 130.02 (C-600, C-700), 130.66 (C-4a00), 132.78 (C-600, C-700),
134.15 (C-300), 138.67, 138.90 (C-3), 139.00 (C-8a00), 142.19 (C-1), 171.53 (C-50),
175.26 (CONH). MS m/z (I, %): 388 [M ? H]? (100). Found, %: C 71.57, H 5.68,
N 10.91. Calculated, %: C 71.30, H 5.46, N 10.85. C23H21N3O3.
N0-(3-Methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-(4-methylphenyl)-5-
oxopyrrolidine-3-carbohydrazide (6c)
Yield 2.6 g (67.0%), m.p. 288–289 °C (from the mixture of 2-propanol and
1
dimethylformamide (1:1)). IR, m: 1643, 1675 (C=O), 3080, 3112, 3177 (NH). H
NMR (300 MHz, DMSO-d6), d: 2.10 (s, 3H, (300-CH3)), 2.27 (s, 3H, (4-CH3)),
2.78–2.95 (m, 2H, CH2CO), 4.01–4.20 (m, 2H, NCH2), 4.30 (br. s, CH), 7.17
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