2372
P. KOPARIR ET AL.
[({4-[3-Methyl-3-(2,4,6-Trimethylphenyl)Cyclobutyl]-1,3-
Thiazol-2-yl}Amino)(4-Nitrophenyl)Methyl]Phosphinic Acid (2b)
Shining white solid, yield 79%, m.p. 357–358 ◦C. IR (KBr, cm−1) υ: 3479 ( OH),
3299 ( NH), 2389 ( P H), 1607 (C N), 1255 ( P O), 1079 ( P O) cm−1. 1H NMR
(400 MHz, CDCl3, Me4Si, δ, ppm): 8.79 (br, 1H, POH), 7.48–8.16 (m, 4H, Ar H), 6.73
(s, 2H, aromatics, in mesitylene), 6.00 (s, 1H, CH S in thiazole ring), 5.43 (br, 1H, NH),
5.11 (d, 1H, PH), 4.78 (d, 1H, CHP), 3.94 (q, 1H, >CH in cyclobutane ring), 2.64 (d, 4H,
CH2 in cyclobutane ring), 2.21 (s, 3H, CH3), 2.16 (s, 6H, CH3), 1.55 (s, 3H, CH3). 13
C
NMR (100 MHz, CDCl3, δ, ppm): 171.9, 166.8, 162.4, 161.2, 157.8, 148.5, 148.0, 139.4,
139.0, 137.6, 133.3, 129.7, 126.9, 124.0, 99.8, 42.2, 31.8, 29.8. 31P NMR (161.9 MHz,
CDCl3, δ, ppm): 28.3; Elemental analysis: C24H28N3O4PS Calculated: C, 59.37; H, 5.81;
N, 8.65. Found: C, 59.47; H, 5.79; N, 8.69.
[(4-Methoxyphenyl)({4-[3-Methyl-3-(2,4,6-Trimethylphenyl)
Cyclobutyl]-1,3-Thiazol-2-yl}Amino)Methyl]Phosphinic Acid (2c)
◦
Yellow solid, yield 48%, m.p. 333–334 C. IR (KBr, cm−1) υ: 3485 ( OH), 3287
( NH), 2392 ( P H), 1609 ( C N), 1254 ( P O), 1082 ( P O) cm−1. 1H NMR (400
MHz, CDCl3, Me4Si, δ, ppm): 8.80 (br, 1H, POH), 6.88–7.21 (m, 4H, Ar H), 6.74 (s, 2H,
aromatics, in mesitylene), 5.99 (s, 1H, CH S in thiazole ring), 5.45 (br, 1H, NH), 5.10 (d,
1H, PH), 4.76 (d, 1H, CHP), 3.92 (q, 1H, >CH in cyclobutane ring), 3.79 (s, 3H, OCH3),
2.63 (d, 4H, CH2 in cyclobutane ring), 2.20 (s, 3H, CH3), 2.15 (s, 6H, CH3), 1.53 (s,
3H, CH3). 13C NMR (100 MHz, CDCl3, δ, ppm): 172.0, 166.9, 163.4, 161.2, 157.8, 148.5,
148.0, 139.8, 138.9, 137.6, 133.4, 129.4, 127.1, 127.0, 100.0, 56.0, 42.2, 38.3, 29.1. 31P
NMR (161.9 MHz, CDCl3, δ, ppm): 28.3; Elemental analysis: C25H31N2O3PS Calculated:
C, 63.81; H, 6.64; N, 5.95. Found: C, 63.79; H, 6.63; N, 6.00.
[(4-Chlorophenyl)({4-[3-Methyl-3-(2,4,6-Trimethylphenyl)
Cyclobutyl]-1,3-Thiazol-2-yl}Amino)Methyl]Phosphinic Acid (2d)
◦
White solid, yield 60%, m.p. 343–344 C. IR (KBr, cm−1) υ: 3498 ( OH), 3282
( NH), 2398 ( P H), 1611 ( C N), 1249 ( P O), 1083 ( P O) cm−1. H NMR
1
(400 MHz, CDCl3, Me4Si, δ, ppm): 8.81 (br, 1H, POH), 7.20–7.31 (m, 4H, Ar H), 6.73
(s, 2H, aromatics, in mesitylene), 6.03 (s, 1H, CH S in thiazole ring), 5.46 (br, 1H, NH),
5.12 (d, 1H, PH), 4.79 (d, 1H, CHP), 3.92 (q, 1H, >CH in cyclobutane ring), 2.63 (d, 4H,
CH2 in cyclobutane ring), 2.20 (s, 3H, CH3), 2.16 (s, 6H, CH3), 1.53 (s, 3H, CH3). 13
C
NMR (100 MHz, CDCl3, δ, ppm):171.8, 166.8, 162.4, 161.2, 157.8, 148.5, 148.0, 139.4,
139.1, 133.3, 129.7, 127.1, 126.8, 100.0, 42.2, 31.8, 26.4, 22.4, 29.2. 31P NMR (161.9
MHz, CDCl3, δ, ppm): 28.4; Elemental analysis: C24H28ClN2O2PS Calculated: C, 60.69;
H, 5.94; N, 5.90. Found: C, 60.71; H, 5.91; N, 5.89.
[(2-Hydroxynaphthalen-1-yl)({[4-(3-Methyl-3-Phenylcyclobutyl)-
1,3-Thiazol-2-yl]Amino})Methyl]Phosphinic Acid (2e)
◦
Yellow solid, yield 48%, m.p. 324–225 C. IR (KBr, cm−1) υ: 3498 ( OH), 3309
( NH), 2401 ( P H), 1602 ( C N), 1258 ( P O), 980 ( P O) cm−1. 1H NMR (400
MHz, CDCl3, Me4Si, δ, ppm): 13.64 (s, 1H, OH), 8.61 (br, 1H, POH), 7.16–7.56 (m, 11H,