P. Molina et al. / Journal of Organometallic Chemistry 584 (1999) 147–158
153
J=1.8 Hz), 4.37 (t, 4H, J=1.8 Hz), 4.19 (s, 10H, 2.34
(m, 4H), 1.41 (m, 2H); 13C-NMR (CDCl3): l 204.0
(CꢀO), 149.6 (q), 136.5 (q, 3JP–C=24.3 Hz), 131.5 (CH,
J=8.0, J=1.0 Hz), 7.47–7.02 (m, 9H), 4.83 (t, 2H,
J=1.9 Hz), 4.57 (t, 2H, J=1.9 Hz), 4.09 (s, 5H);
13C-NMR (CDCl3): l 201.5 (CꢀO), 168.0 (CꢀO), 152.5
(q), 141, 7 (q), 138.3 (q), 137.6 (q), 133.2 (CH), 132.7
(CH), 130.5 (CH), 129.0 (CH), 127.0 (CH), 126.9 (q),
123.5 (CH), 123.1 (CH), 122.1 (CH), 121.9 (CH), 121.1
(CH), 120.2 (CH), 119.1 (q), 78.6 (ipso-Fec), 73.3 (2×
CH, C5H4), 72.0 (2×CH, C5H4), 70.3 (5×CH, C5H5);
EI MS: m/z (%) 525 (M+, 53), 450 (100), 389 (54),
340 (58), 248 (16), 237 (32), 145 (28), 92 (85), 65 (35),
and 55 (17). Anal. Calc. for C31H23FeN3O2: C, 70.87;
H, 4.41; N 8.00. Found: C, 70.74; H, 4.20; N, 7.96%.
4
2JP–C=9.4 Hz), 131.3 (CH, JP–C=2.8 Hz), 130.6 (q,
3
1JP–C=96.0 Hz), 139.9 (CH), 128.5 (CH, JP–C=11.6
Hz), 127.8 (CH, 4JP–C=2.9 Hz), 121.5 (CH,
3JP–C=11.6 Hz), 116.1 (CH), 80.8 (ipso-Fec), 71.4
(2×CH, C5H4), 71.2 (2×CH, C5H4), 69.8 (5×CH,
C5H5), 26.5 (2×CH2, 1JP–C=65.2 Hz), 15.28 (CH2,
2JP–C=16.4 Hz); 31P-NMR (CDCl3): l 4.57 ppm; MS
FAB+1019 (M+ +1, 100). Anal. Calc. for
C61H52Fe2N2O2P2: C, 71.92; H, 5.14; N, 2.75. Found:
C, 71.70; H, 5.26; N, 2.60%.
3.5.2. Compound 13b (Ar=4-H3CO–C6H5)
Yield 49%; m.p. 99–100°C; IR (Nujol): w 3313,
3.4.2. Bis(iminophosphorane) 9
Yield 94%; m.p. \320°C (orange prisms, from
dichloromethane:ethyl ether); IR (Nujol): w 1643, 1590,
1474, 1455, 1439, 1350, 1300, 1115, 1056, 1034, 1024,
1707, 1656, 1585, 1515, 1438, 1297, 1246, 1175, 1041,
1
836 and 747 cm−1; H-NMR (CDCl3): l 10.59 (s, 1H),
8.45 (d, 1H, J=8.4 Hz), 8.35 (d, 1H, J=8.4 Hz), 7.93
(d, 1H, J=7.8 Hz), 7.68 (d, 1H, J=8.1 Hz), 7.43 (t,
1H, J=7.0 Hz), 7.40 (t, 1H, J=7.0 Hz), 7.22 (d, 2H,
J=8.7 Hz), 7.10 (t, 1H, J=7.5 Hz), 7.04 (t, 1H,
J=7.5 Hz), 6.77 (d, 2H, J=8.7 Hz), 4.82 (t, 2H,
J=1.8 Hz), 4.56 (t, 2H, J=1.8 Hz), 4.03 (s, 5H), 3.71
(s, 3H); 13C-NMR (CDCl3): l 201.5 (CꢀO), 167.8
(CꢀO), 156.5 (q), 153.4 (q), 141.7 (q), 137.7 (q), 133.1
(CH), 132.7 (CH), 131.0 (q), 130.4 (CH), 126.9 (CH),
126.8 (q), 123.5 (CH), 122.9 (CH), 122.0 (CH), 121.8
(CH), 121.1 (CH), 119.2 (q), 78.6 (ipso-Fec), 73.3 (2×
CH, C5H4), 72.0 (2×CH, C5H4), 70.4 (5×CH, C5H5),
55.5 (CH3O); EI MS: m/z (%) 555 (M+, 8), 450 (100),
424 (12), 385 (47), 371 (23), 342 (12), 268 (60), 146
(20), 123 (74) and 108 (85). Anal. Calc. for
C32H25FeN3O3: C, 69.20; H, 4.54; N 7.57. Found: C,
69.35; H, 4.40; N, 7.24%.
748, 721, 696 and 657 cm−1 1H-NMR (CD2Cl2): l
;
7.48–7.26 (m, 22H), 6.88 (t, 2H, J=7.6 Hz), 6.66 (t,
2H, J=7.3 Hz), 6.19 (d, 2H, J=7.9 Hz), 5.31 (t, 4H,
J=1.6 Hz), 4.81 (t, 4H, J=1.8 Hz), 4.47 (t, 4H,
J=1.8 Hz), 4.23 (t, 4H, J=1.6 Hz), 4.21 (s, 10H);
13C-NMR (CD2Cl2): l 181.8 (CꢀO), 149.4 (q), 132.3
(CH, 2JP–C=10.1 Hz), 132.1 (q, 1JP–C=102.2 Hz),
131.8 (CH, 4JP–C=2.5 Hz), 129.9 (CH), 128.7 (CH,
3JP–C=12.1 Hz), 127.9 (CH, 4JP–C=2.5 Hz), 121.7
(CH, 3JP–C=11.0 Hz), 116.4 (CH), 81.4 (ipso-Fec),
2
1
74.7 (CH, C5H4, JP–C=9.9 Hz), 74.2 (ipso-Fec, JP–
3
C=115.9 Hz), 74.0 (CH, C5H4, JP–C=12.2 Hz), 72.1
(2×CH, C5H4), 71.5 (2×CH, C5H4), 70.2 (5×CH,
C5H5); 31P-NMR (CDCl3):
l
2.48 ppm; MS
FAB+1161 (M+ +1, 100). Anal. Calc. for
C68H54Fe3N2O2P2: C, 70.37;H, 4.69; N, 2.41. Found:
C, 70.54; H, 4.46; N, 2.30%.
3.5.3. Compound 13c (Ar=4-H3C–C6H5)
Yield 45%; m.p. 110–112°C; IR (Nujol): w 3303,
3.5. General procedure for the preparation of 2-
arylamino-3-(o-ferrocenecarbonyl)phenyl-3H-
quinazolin-4-ones 13
1717, 1667, 1584, 1506, 1456, 1378, 1295, 1245, 1118,
1
1057, 835 and 757 cm−1; H-NMR (CDCl3): l 10.72
(s, 1H), 8.52 (d, 1H, J=8.3 Hz), 8.43 (d, 1H, J=8.3
Hz), 8.02 (dd, 1H, J=7.8, J=1.3 Hz), 7.77 (dd, 1H,
J=7.9, J=1.1 Hz), 7.52 (t, 1H, J=7.0 Hz), 7.48 (t,
1H, J=7.1 Hz), 7.28 (d, 2H, J=8.3 Hz), 7.11–7.06
(m, 4H), 4.90 (t, 2H, J=1.8 Hz), 4.64 (t, 2H, J=1.8
Hz), 4.16 (s, 5H), 2.16 (s, 3H); 13C-NMR (CDCl3): l
201.6 (CꢀO), 168.0 (CꢀO), 152.9 (q), 141.7 (q), 137.6
(q), 133.3 (q), 133.2 (CH), 132.7 (CH), 130.5 (CH),
129.5 (CH), 127.0 (CH), 126.9 (q), 123.0 (CH), 122.1
(CH), 121.8 (CH), 121.1 (CH), 120.9 (CH), 119.4 (q),
78.6 (ipso-Fec), 73.3 (2×CH, C5H4), 72.0 (2×CH,
C5H4), 70.3 (5×CH, C5H5), 20.1 (CH3); EI MS: m/z
(%) 539 (M+, 6), 450 (100), 424 (78), 385 (36), 359
(85), 341 (52), 293 (33), 252 (12), 146 (13), 133 (36),
121 (24) and 107 (51). Anal. Calc. for C32H25FeN3O2:
C, 71.25; H, 4.67; N 7.79. Found: C, 71.12; H, 4.70;
N, 7.58%.
To a solution of iminophosphorane 7 (0.4 g, 0.58
mmol) in anhydrous dichloromethane (20 ml) the ap-
propriate isocyanate (0.58 mmol) was added. The re-
sultant mixture was stirred at r.t. under nitrogen for 96
h. The solution was concentrated to dryness and the
residue was chromatographed on a silica gel column
using ethyl acetate:n-hexane (3:2) as eluent. The fol-
lowing products were isolated after recrystallization
from dichloromethane:diethyl ether (1:1).
3.5.1. Compound 13a (Ar=C6H5)
Yield 40%; m.p. 98–100°C; IR (Nujol): w 3332,
1709, 1669, 1599, 1517, 1502, 1450, 1298, 1243 and 761
1
cm−1; H-NMR (CDCl3): l 10.72 (s, 1H), 8.45 (dd,
1H, J=8.4, J=0.8 Hz), 8.38 (dd, 1H, J=8.4, J=0.8
Hz), 7.95 (dd, 1H, J=7.9, J=1.5 Hz), 7.68 (dd, 1H,