JOURNAL OF CHEMICAL RESEARCH 2008 69
139.30, 157.91; MS m/z (%) 530 (M+ + 2, 33), 529 (M+ + 1, 14), 528
(M+,42), 429 (11), 394 (48), 318 (13), 151 (87), 139 (48), 111 (100),
102 (23), 90 (14), 75 (51), 51 (13). Anal. Calcd. for C22H18Cl2N8O4
(528): C, 49.92; H, 3.43; Cl, 13.40; N, 21.17. Found: C, 50.05; H,
3.64; Cl, 13.55; N, 21.22%.
422 (9), 397 (4), 152 (39), 137 (69), 111 (52), 91 (56), 64 (55), 50
(45). Anal. Calcd. for C30H20N8O2 (524): C, 68.69; H, 3.84; N, 21.36.
Found: C, 68.60; H, 3.72; N, 21.47%.
5,6-Dibenzoyl-3,8-di(4-nitrophenyl)-1,2,3,4,5a,7,8,8b-octaaza-
acenaphthylene (5l): Pale brown solid (AcOH), (1.23 g, 40%),
m.p.360°C,IRν(cm-1)1661(C=O),1594(C=N);1HNMR(DMSO-d6)
d 7.3–8.0 (m, 10H, ArH), 8.1 (d, J = 9 Hz, 4H, ArH), 8.3 (d, J = 9 Hz,
4H, ArH); MS m/z (%) 614 (M+,7), 485 (3), 309 (4), 131 (11), 105
(100), 77 (34), 62 (5), 51 (17). Anal. Calcd. for C30H18N10O6 (614):
C, 58.63; H, 2.95; N, 22.79. Found: C, 58.36; H, 3.07; N, 22.49%.
Crystal and molecular structure of compound 5c:All crystallographic
data have been deposited at the Cambridge Crystallographic Data
Centre as supplementary publication no. CCDC – 666041. Copies
of the data can be obtained free of charge on application to CCDC,
12 Union Road, Cambridge CB2 1EZ, UK. All diagrams and
calculations were performed using maXus (Bruker Nonius, Delft &
MacScience, Japan. The crystal system is triclinic and the space group
is P1. Unit cell: a = 10.0002 (3)Å; b = 11.0762 (5)Å, c = 2.1798 (6)Å,
α = 71.462 (2)°, β = 65.781 (2)°, γ = 63.179 (2)°, V = 1083.26 (8)Å3,
Z = 2. Crystallographic density, Dx = 1.412 Mg m-3 and l = 0.71073.
The R-factors are: Rint = 0.044, R(all) = 0.225, R(gt) = 0.154, wR(ref)
= 0.341, wR(all) = 0.360 and wR(gt) = 0.342.
5,6-Diethoxycarbonyl-3,8-di(4-nitrophenyl)-1,2,3,4,5a,7,8,8b-
octaaza-acenaphthylene (5f): Yellow solid (AcOH), (1.51, g, 55%),
m.p.220°C, IR ν (cm-1) 1731 (C=O),1591 (C=N); 1H NMR (DMSO-
d6) d 1.2 (t, J = 7 Hz, 6H, 2 CH3), 4.2 (q, J = 7 Hz, 4H, 2 CH2), 7.5
(d, J = 8 Hz, 4H, ArH), 8.2 (d, J = 8 Hz, 4H, ArH). MS m/z (%) 552
(M+ + 2, 9), 551 (M+ + 1, 22), 550 (M+,29), 404 (11), 264 (11), 217
(20), 189 (20), 162 (23), 149 (24), 132 (24), 121 (41), 115 (18), 101
(30), 89 (100), 75 (75), 50 (58). Anal. Calcd. for C22H18N10O8 (550):
C, 48.01; H, 3.30; N, (25.45. Found: C, 48.05; H, 3.43; N, 25.30%.
5,6-Diphenylcarbamoyl-3,8-diphenyl-1,2,3,4,5a,7,8,8b-octa-aza-
a-cenaphthylene (5g): Yellow solid (AcOH), (1.53 g, 55%), m.p.
1
240°C, IR ν (cm-1) 3295 (NH),1660 (C=O),1595 (C=N); H NMR
(DMSO-d6) d 7.1–8.1 (m, 20H, ArH), 10.8 (s, 2H, 2 NH); MS m/z
(%) 555 (M+ + 1, 7), 554 (M+,19), 408 (11), 288 (12), 220 (12), 144
(12), 119 (45), 91 (48), 77 (100), 65 (49), 51 (39). Anal. Calcd. for
C30H22N10O2 (556): C, 64.97; H, 4.00; N, 25.26. Found: C, 64.80; H,
4.15; N, 25.09%.
5,6-Diphenylcarbamoyl-3,8-di(4-methylphenyl)-1,2,3,4,5a,7,8,8b-
octaaza-acenaphthylene (5h): Yellow solid (AcOH), (1.75 g, 60%),
m.p. 330°C, IR ν (cm-1) 3282 (NH),1660 (C=O),1597 (C=N);
1H NMR (DMSO-d6) d 2.3 (s, 6H, 2 CH3), 7.1–7.3 (m, 10H, ArH),
7.6 (d, J = 8 Hz, 4H, ArH), 8.0 (d, J = 8 Hz, 4H, ArH), 10.8 (s, 2H,
2 NH); MS m/z (%) 583 (M+ + 1, 3), 582 (M+,7), 436 (5), 316 (6),
278 (6), 186 (7), 146 (11), 132 (38), 119 (72), 91 (100), 77 (26), 64
(45), 51 (32). Anal. Calcd. for C32H26N10O2 (582): C, 65.97; H, 4.50;
N, 24.04, Found: C, 65.90; H, 4.75; N, 24.06%.
5,6-Diphenylcarbamoyl-3,8-di(4-chlorophenyl)-1,2,3,4,5a,7,8,8b-
octaaza-acenaphthylene (5i): Yellow solid (AcOH), (1.49 g, 45%),
m.p. 302°C, IR ν (cm-1) 3265 (NH),1668 (C=O),1596 (C=N);
1H NMR (DMSO-d6) d 7.5–7.8 (m, 10H, ArH), 8.1 (d, J = 9 Hz, 4H,
ArH), 8.2 (d, J = 8 Hz, 4H, ArH), 11.1 (s, 2H, 2 NH); MS m/z (%)
626 (M+ + 2, 14), 625 (M+ + 1, 9), 624 (M+, 24), 441 (30), 322 (14),
299 (13), 206 (19), 151 (37), 119 (100), 91 (83), 77(60), 65 (62), 51
(39). Anal. Calcd. for C30H20Cl2N10O2 (622): C, 57.80; H, 3.23; Cl,
11.37; N, 22.47. Found: C, 57.70; H, 3.30; Cl, 11.21; N, 22.26%.
5,6-Diphenylcarbamoyl-3,8-di(4-nitrophenyl)-1,2,3,4,5a,7,8,8b-
octaaza-acenaphthylene (5j): Yellow solid (AcOH), (1.71 g, 53%),
m.p. 240°C, IR ν (cm-1) 3424 (NH),1657 (C=O),1602 (C=N);
1H NMR (DMSO-d6) d 7.3–7.8 (m, 10H, ArH), 8.1 (d, J = 8 Hz, 4H,
ArH), 8.2 (d, J = 8 Hz, 4H, ArH),10.2 (s, 2H, 2 NH); MS m/z (%)
651 (M+ + 7,1), 639 (1), 604 (1), 569 (1), 445 (1), 382 (1), 284 (3),
242 (2), 179 (8), 159 (6), 154 (4), 150 (4), 119 (36), 90 (31), 77 (15),
63 (100), 53 (40). Anal. (Calcd. for C30H20N12O6 (644): C, 55.90; H,
3.13; N, 26.08. Found: C, 55.80; H, 3.05; N, 26.15%.
Paper 07/4998
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5,6-Dibenzoyl-3,8-diphynyl-1,2,3,4,5a,7,8,8b-octaaza-
acenaphthylene(5k):Yellowsolid(AcOH), (1.00g, 40%), m.p. 260°C,
IR ν (cm-1) 1669 (C=O),1599 (C=N); 1H NMR (DMSO-d6) d 7.1–8.2
(m, ArH); MS m/z (%) 526 (M+ + 2,17), 525 (M+ + 1,22), 524 (M+,1),
PAPER: 07/4998