JOURNAL OF CHEMICAL RESEARCH 2007 667
(m, 2H, ArH), 7.57–7.52 (m, 2H, ArH), 7.48–7.32 (m, 8H, ArH),
7.24–7.18 (m, 2H, ArH), 7.16–7.12 (m, 2H, ArH), 7.04–6.92 (m,
2H, ArH), 4.70 (s, 2H, CH2-benzoyl). 13C NMR (CDCl3): δ = 196.0,
193.2 (CO), 159.8, 158.2 (C=N), 140.0 (N-Ph C), 139.0, 138.8, 138.4
(Ph C), 128.6, 128.4, 128.0, 127.8 (Ar o-2CH), 127.6, 127.2, 127.0,
126.8 (Ar m-2CH), 126.6, 126.4, 126.2, 126.0 (Ar p-CH), 37.4 (CH2-
benzoyl). MS (EI, 70 eV): m/z (%) = 445 [M+] (14), 248 (66), 197
(18), 180 (92), 118 (30), 91 (24), 105 (100), 77 (54). C29H23N3O2
(445.53): Calcd. C, 78.18; H, 5.20; N, 9.43. Found: C, 78.04; H, 5.30;
N, 9.40.
(2Z)-2-({(E}[4-Methylphenylamino]phenylmethylene}hydrazono)-
1,4-diphenylbutan-1,4-dione (6c): Yellow crystals (0.40 g. 88%);
Rf = 0.45 (CH2Cl2), m.p. 196°C (methanol). IR (KBr): n = 3210 (m,
NH), 3065-3010 (m, Ar-CH), 2986–2870 (m, aliph-CH), 1708–1688
(C=O), 1610, 1600 (s, C=N), 1594 (s, C=C) cm-1. UV (CH3CN): λmax
(log ε) = 400 (4.06). 1H NMR (CDCl3): δ = 8.22 (s, 1H, NH), 8.15–
8.06 (m, 2H, ArH), 7.60–7.50 (m, 4H, ArH), 7.40–7.25 (m, 7H, ArH),
7.22–7.10 (m, 4H, ArH), 7.04–6.92 (m, 2H, ArH), 4.70 (s, 2H, CH2-
benzoyl), 2.38 (s, 3H, CH3). 13C NMR (CDCl3): δ = 196.2, 193.0
(CO), 160.2, 157.5 (C=N), 140.0 (N-Ph C), 139.2, 138.2, 138.0,
137.6 (Ph C), 128.6, 128.0, 127.6, 127.0 (Ar o-2CH), 126.8, 126.6,
126.4, 126.2 (Ar m-2CH), 125.8, 125.4, 125.2 (Ar p-CH), 37.8 (CH2-
benzoyl), 32.8 (CH3). MS (EI, 70 eV): m/z (%) = 459 [M+] (24), 248
(60), 211 (24), 180 (80), 118 (34), 105 (100), 77 (50). C30H25N3O2
(459.55): Calcd. C, 78.41; H, 5.48; N, 9.14. Found: C, 78.60; H, 5.40;
N, 9.10.
7.60–7.30 (m, 9H, ArH), 7.24–7.16 (m, 5H, ArH), 6.80–6.76 (m, 2H,
ArH), 6.72 (d, 1H, J = 1.3 Hz, ArH), 4.68 (s, 2H, CH2-benzoyl). 13
C
NMR (CDCl3): δ = 196.2, 194.0 (CO), 160.2, 157.6 (C=N), 140.4
(N-Ph C), 138.2, 138.0, 137.8 (Ph C), 133.2 (Cl-Ph C), 128.0, 127.6,
127.4 (Ar o-2CH), 127.2, 127.0, 126.8, 126.6 (Ar m-2CH), 126.0,
125.8, 125.4 (Ar p-CH), 122.2 (Cl-Ph o-2CH), 37.4 (CH2-benzoyl).
MS (EI, 70 eV): m/z (%) = 481 [M + 2] (30), 479 [M+] (100), 477
(28), 251 (56), 248 (60), 233 (24), 231 (24), 128 (14), 126 (18), 118
(40), 107 (75), 105 (78), 77 (32). C29H22ClN3O2 (479.97): Calcd. C,
72.57; H, 4.62; Cl, 7.39; N, 8.75. Found: C, 72.50; H, 4.60; Cl, 7.30;
N, 8.70.
Received 31 October 2007; accepted 7 December 2007
Paper 07/4926
doi: 10.3184/030823407X268340
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(2Z)-2-({(E}[4-Chlorophenylamino]phenylmethylene}hydrazono)-
1,4-diphenylbutan-1,4-dione (6d): Pale yellow crystals (0.36 g,
75%); Rf = 0.25 (CH2Cl2), m.p. 172°C (ethanol). IR (KBr): n = 3230
(m, NH), 3060–3010 (m, Ar-CH), 1706–1690 (s, C=O), 1618, 1612
(s, C=N), 1598 (s, C=C) cm-1. UV (CH3CN): λmax (log ε) = 398 (3.8).
1H NMR (CDCl3): δ = 8.18 (s, 1H, NH), 8.00–7.96 (m, 2H, ArH),
7.60–7.36 (m, 7H, ArH), 7.26–7.10 (m, 6H, ArH), 6.90–6.86 (m, 2H,
7
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ArH), 6.70 (d, 2H, J = 8.0 Hz, ArH), 4.68 (s, 2H, CH2-benzoyl). 13
C
NMR (CDCl3): δ = 196.0, 193.2 (CO), 160.0, 157.4 (C=N), 140.0
(N-Ph C), 138.0, 137.8, 137.5 (Ph C), 134.0 (Cl-Ph C), 128.0, 127.6,
127.2 (Ar o-2CH), 127.0, 126.8, 126.6, 126.4 (Ar m-2CH), 125.8,
125.6, 125.2 (Ar p-CH), 124.5 (Cl-Ph 2CH), 37.6 (CH2-benzoyl).
MS (EI, 70 eV): m/z (%) = 481 [M + 2] (32), 479 [M+] (100), 477
(26), 251 (54), 248 (56), 233 (22), 231 (20), 128 (23), 126 (26), 118
(38), 107 (72), 105 (76), 77 (36). C29H22ClN3O2 (479.97): Calcd. C,
72.57; H, 4.62; Cl, 7.39; N, 8.75. Found: C, 72.40; H, 4.68; Cl, 7.35;
N, 8.66.
(2Z)-2-({(E}[3-Chlorophenylamino]phenylmethylene}hydrazono)-
1,4-diphenylbutan-1,4-dione (6e): Pale yellow crystals (0.34 g, 70%);
Rf = 0.25 (CH2Cl2), m.p. 210–212°C (ethanol). IR (KBr): n = 3220
(m, NH), 3060–3010 (m, Ar-CH), 1708–1686 (s, C=O), 1610, 1608
(s, C=N), 1598 (m, C=C) cm-1. UV (CH3CN): λmax (log ε) = 390 (3.6).
1H NMR (CDCl3): δ = 8.20 (s, 1H, NH), 8.00–7.97 (m, 2H, ArH),
22 J.J. Zhang and G.B. Schuster J. Am. Chem. Soc. 1989, 111, 7.
PAPER: 07/4926