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3.71 (3H, d, J = 12.5 Hz, POCH3), 3.86 (3H, s, Ar-OCH3), 5.21 (1H, d, J = 8.6 Hz,
P-C-H), 5.25 (1H, s, Ar-OH), 6.53–6.98 (3H, m, Ar H). 13C-NMR (100 MHz, CDCl3)
δ: 52.5 (d, J = 7.2 Hz, P OCH3), 55.9 (d, J = 7.7 Hz, P-OCH3), 56.1 ( Ar OCH3),
59.2 (d, J = 157.3 Hz, P CH), 112.7 (C-2), 115.3 (C-5), 120.37 (C-6), 129.8 (C-1), 147.1
(C-4), 147.4 (C-3). 31P-NMR (162.0 MHz, CDCl3) δ: 23.4. MS (ESI): m/z 263 [M+H]+;
anal. calcd. for C10H15O6P: C,45.81; H, 5.78. Found: C, 45.78; H, 5.74.
Dimethyl(hydroxy(4-(pyrrolidin-1-yl)phenyl)methyl)phosphonate (3e).
Reddish brown semisolid, yield: 90%. IR (KBr) (υmax, cm−1): 3468 (brs, OH), 1251 (P =
1
O), 1021 (P O C). H-NMR (400 MHz, CDCl3) δ: 1.99 (4H, m, pyrrolidine H C-3,4),
3.31 (4H, m, pyrrolidine H C-2,5), 3.65 (3H, d, J = 12.5 Hz, POCH3), 3.74 (3H, d, J
= 12.6 Hz, POCH3), 4.76 (1H, d, J = 7.9 Hz, P C H), 6.54–7.29 (4H, m, Ar H).
13C NMR (100 MHz, CDCl3) δ: 25.5 (C-31, 41), 47.6 (C-21,51), 53.6 (d, J = 8.3 Hz,
P OCH3), 53.7 (d, J = 7.6 Hz, P OCH3), 57.9 (d, J = 159.9 Hz, P CH), 111.1 (C-3,5),
119.6 (C-1), 129.4 (C-2,6), 148.2 (C-4). 31P NMR (162.0 MHz, CDCl3) δ: 22.5. MS
(ESI): m/z 286 [M+H]+; anal. calcd. for C13H20NO4P: C,54.73; H, 7.08. Found: C, 54.56;
H, 7.00.
Dimethyl(hydroxy(1H-imidazol-4-yl)methyl)phosphonate (3f). Pink solid,
yield: 93%, Mp:120-122◦C. IR (KBr) (υmax, cm−1): 3267 (brs, OH), 1214 (P O), 1021
(P O C). 1H-NMR (400 MHz, CDCl3) δ: 3.32 (3H, d, J = 12.4 Hz, POCH3), 3.67 (3H,
d, J = 12.5 Hz, POCH3), 5.23 (1H, d, J = 8.3 Hz, P C H), 7.24–8.70 (2H, m, -imidazole
H), 13.00 (1H, s, NH). 13C NMR (100 MHz, CDCl3) δ: 51.7 (d, J = 8.3 Hz, P-OCH3),
58.2 (d, J = 8.2 Hz, P-OCH3), 60.4 (d, J = 161.3 Hz, P C), 119.2 (C-5), 122.1 (C-4),
136.4 (C-2). 31P-NMR (162.0 MHz, CDCl3) δ: 19.8. MS (ESI): m/z 207 [M+H]+; anal.
calcd. for C6H11N2O4P: C, 34.68; H, 5.38. Found: C, 34.65; H, 5.34.
Dimethyl(hydroxy(1H-pyrrol-2-yl)methyl)phosphonate (3g). Black semi-
solid, yield: 88%. IR (KBr) (υmax, cm−1): 3165 (brs, OH), 1231 (P O), 1014 (P O C).
1H-NMR (400 MHz, CDCl3) δ: 3.59 (3H, d, J = 12.2 Hz, POCH3), 3.67 (3H, d, J =
12.5 Hz, POCH3), 5.11 (1H, s, NH), 5.13 (1H, d, J = 7.8 Hz, P C H), 5.02–6.84 (3H, m,
pyrrole-H).13C-NMR (100 MHz, CDCl3) δ: 53.5 (d, J = 6.9 Hz, P OCH3), 56.5 (d, J =
8.1 Hz, P OCH3), 60.0 (d, J = 157.8 Hz, P CH), 105.3 (C-3), 108.6 (C-4); 117.1 (C-5),
132.2 (C-2). 31P NMR (162.0 MHz, CDCl3) δ: 21.6. MS (ESI): m/z 206 [M+H]+; anal.
calcd. for C7H12NO4P: C,40.58; H, 5.96. Found: C, 40.44; H, 5.64.
Dimethyl(hydroxy(pyridin-4-yl)methyl)phosphonate (3h). Orange semi-
solid, yield: 91%. IR (KBr) (υmax, cm−1): 3359 (brs, OH), 1227 (P O), 1037 (P O C).
1H-NMR (400 MHz, DMSO-d6) δ: 3.31 (3H, d, J = 12.8 Hz, POCH3), 3.37 (3H, d, J =
12.7 Hz, POCH3), 4.98 (1H, d, 8.4 Hz, P C H), 8.03-8.90 (4H, m, Ar H). 13C-NMR
(100 MHz, DMSO-d6) δ: 52.8 (d, J = 7.3 Hz, P-OCH3), 53.9 (d, J = 7.9 Hz, P OCH3),
59.1 (d, J = 160.2 Hz, P CH), 124.4 (C-2,6), 146.1 (C-1), 149.4 (C-3,5). 31P NMR
(162.0 MHz, DMSO-d6) δ: 19.1 (P = O). MS (ESI): m/z 218 [M+H]+; anal. calcd. for
C8H12NO4P: C,44.68; H, 5.57. Found: C, 44.65; H, 5.54.
Dimethyl(hydroxy(thiophene-2-yl)methyl)phosphonate
(3i). Greenish
brown semisolid, yield: 85%. IR (KBr) (υmax, cm−1): 3123 (brs, OH), 1227 (P O), 1019
1
(P O C). H-NMR (400 MHz, CDCl3) δ: 3.63 (3H, d, J = 12.3 Hz, POCH3), 3.68
(3H, d, J = 12.4 Hz, POCH3), 5.42 (1H, d, J = 7.8 Hz, P C H), 6.43–7.58 (3H, m,
thiophene-H).13C NMR (100 MHz, CDCl3) δ: 53.1 (d, J = 6.9 Hz, P OCH3), 56.9 (d,