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R. MOHEBAT ET AL.
m, aromatic), 9.18 (1H, br, NH) ppm. 13C NMR (125.7 MHz, d6-DMSO): d 13.88
2
=
(CH3), 27.95 and 30.17 (2NCH3), 38.43 (CH, d, JPC ¼ 14.9 Hz), 41.32 (C P,
d, JPC ¼ 125 Hz), 60.40 (OCH2), 84.40 (d,3JPC ¼ 12 Hz, C C-NH), 125.12 (C
,
,
1
ipso
=
d, JPC ¼ 91.0 Hz), 129.36 (Cmeta, d, JPC ¼ 11.8 Hz), 132.91 (Cpaea), 133.67 (Cortho
31
1
3
2
2
=
=
d, JPC ¼ 9.9 Hz), 148.33 (C C-NH), 151.27 and 160.78 (2C O), 165.42 (d, JPC
¼
=
=
15.3 Hz, C O), 174.89 (C O) ppm. P NMR (d6-DMSO): d ¼ 20.12 ppm.
Di-tert-butyl-2-(6-amino-1,3 dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyridin-
5-yl)-3-(triphenyl-k5-phosphanylidene)succinate (5). White power; yield (73%);
mp ¼ 179–181 ꢁC. IR (KBr) (nmax cmꢀ1): 3345 (NH2), 1722, 1605 (C O). Analyst:
=
calcd. for C36H42N3O6P: C, 67.17; H, 6.58; N, 6.53%. Found: C, 66.90; H, 6.71;
1
N, 6.64%. MS (m=z, %): 643 (Mþ, 8). H NMR (500 MHz, d6-DMSO): d 0.84 and
3
1.45 (18H, 2 s, 2 t-Bu), 3.06 and 3.38 (6H, 2 s, 2NCH3), 4.15 (1H, d, JHP ¼ 18.8 Hz,
Hz, CH), 7.20 (2H, br, NH2), 7.48–7.67 (15H, m, aromatic), 13C NMR (125.7 MHz,
d6-DMSO): d 25.99 and 28.78 (6CH3), 28.24 and 29.00 (2NCH3), 38.60 (CH, d,
2
1
=
JPC ¼ 13.8 Hz), 40.90 (C P, d, JPC ¼ 125 Hz), 77.06 and 79.35 (2C), 89.04
(C C-NH2), 127.52 (Cipso, d, JPC ¼ 90.2 Hz), 129.38(Cmeta, d, JPC ¼ 11.6 Hz),
1
3
=
132.03 (Cpara), 133.88 (Cortho, d, JPC ¼ 9.9 Hz), 151.64 (C C-NH2), 152.74 and
2
=
2
3
=
=
=
161.25 (C O), 170.95 (C O, d, JPC ¼ 15.3 Hz), 173.03 (C O, d, JPC ¼ 11.3 Hz)
ppm. 31P NMR (d6-DMSO): d 20.85 ppm.
Dimethyl-2-(6-amino-2,4-dihydroxo-pyridin-5-yl)-3-(triphenyl-k5-
phosphanylidene)succinate (7a). White power; yield (88%); mp 185–187 ꢁC; IR
(KBr) (nmax cmꢀ1): 3345 (NH2), 1733, 1688 (C O). Analyst: calcd. for
C28H26N3O6P: C, 63.27; H, 4.93; N, 7.91%. Found: C, 63.39; H, 5.08; N, 7.78%.
=
1
MS (m=z, %): 531 (Mþ, 5). H NMR (500 MHz, d6-DMSO): d 3.05 and 3.65 (6H,
3
2 s, 2OCH3), 4.82 (1H, d, JHP ¼ 16 Hz, CH), 7.60 (1H, s, NH), 7.89 (1H, s, NH),
7.60–7.90 (15H, m, aromatic), 10.98 (2H, s, NH2).13C NMR (125.7 MHz, d6-
1
=
DMSO): d 40.08 (C P, d, JPC ¼ 125 Hz), 50.04 and 52.56 (2OCH3), 58.48 (CH,
2
1
d, JPC ¼ 16.2 Hz), 100.77 (C C-NH2), 125.35 (Cipso, d, JPC ¼ 91.2 Hz), 129.30
=
(Cmeta, d, JPC ¼ 11.3 Hz), 132.72 (Cpara), 133.07 (Cortho, d, JPC ¼ 9.0 Hz), 143.07
3
2
3
=
=
=
(C C-NH2), 150.32 and 150.39 (2C O), 169.54 (C O, d, JPC ¼ 12.5 Hz),
170.67(C O) ppm. 31P NMR (d6-DMSO): d 24.29 ppm.
=
Di-tert-butyl-2-(6-amino-2,4-dihydroxo-pyridin-5-yl)-3-(triphenyl-k5-
phosphany lidene)succinate (7b). White power; yield (70%); mp 180–182 ꢁC; IR
(KBr) (nmax cmꢀ1): 3345 (NH2), 1722, 1692 (C O). Analyst: calcd. for
C34H38N3O6P: C, 66.33; H, 6.22; N, 6.83%. Found: C, 66.42; H, 6.07; N, 6.70%.
=
MS (m=z, %): 615 (Mþ, 7). 1H NMR (500 MHz, d6-DMSO): d 1.43 and 1.45
3
(18H, 2 s, 6CH3), 4.72 (1H, d, JHP ¼ 16.0 Hz, CH), 7.59 (1H, s, NH), 7.48–7.67
(15H, m, aromatic), 7.91 (1H, s, NH), 11.02 (1H, s, NH2). 13C NMR (125.7 MHz,
1
=
d6-DMSO): d 28.09 and 28.21 (6CH3), 40.10 (C P, d, JPC ¼ 125 Hz), 59.37 (CH,
2
d, JPC ¼ 16.8 Hz,), 77.33 and 81.04 (2C), 100.65 (C C-NH2), 126.35 (Cipso, d,
=
1JPC ¼ 91.5 Hz), 129.33 (Cmeta, d, JPC ¼ 11.1 H,), 130.78 (Cpara), 131.75 (Cortho
,
3
d,2JPC ¼ 9.1 Hz), 150.73 (C C-NH2), 151.95 and 164.75 (2C O), 169.12 (C O, d,
=
=
=
JPC ¼ 12.8 Hz), 170.83 (C O) ppm. 31P NMR (d6-DMSO): d 24.08 ppm.
2
=