Molecular Diversity
Diethyl((3‑bromophenyl)((5‑(2‑oxo‑2H‑chromen‑3‑yl)thi‑
azol‑2‑yl)amino)methyl)phosphonate (IV)g White solid.
Recrystallized from EtOH. Yield: 90%; mp: 215.4–216.6 °C;
21.39. Anal. Calcd. for C24H25N2O6PS (%): C, 57.59; H,
5.03; N, 5.60 Found: C, 57.48; H, 5.04; N, 5.52.
1
IR (KBr,cm−1): 3427.75, 1723.27, 1540.45, 1222.12; H
Diethyl((4‑methoxyphenyl)((5‑(2‑oxo‑2H‑chromen‑3‑yl)thi‑
azol‑2‑yl)amino)methyl)phosphonate (IV)j Yellow powder.
Recrystallized from EtOH. Yield: 76%; mp: 236.8–237 °C;
NMR (400 MHz, DMSO-d6) δ=8.80 (dd, J=9.6, 4.0, 1H),
8.68 (s, 1H), 7.98 – 7.73 (m, 2H), 7.69 – 7.56 (m, 3H),
7.51 (d, J=8.1, 1H), 7.39 (dt, J=21.8, 7.8, 3H), 5.75 (dd,
J=21.9, 9.6, 1H), 4.19 – 3.82 (m, 5H), 1.15 (dt, J =38.5,
7.1, 6H). 13C NMR (101 MHz, DMSO-d6) δ = 166.43 (d,
JC–P = 11.3 Hz), 159.19, 152.72, 143.14, 139.61, 139.13,
131.97, 131.50 (d, JC–P =5.5 Hz), 130.99 (d, JC–P =2.7 Hz),
130.77, 129.13, 127.89 (d, JC–P =5.7 Hz), 125.15, 121.91
(d, JC–P =2.4 Hz), 120.78, 119.86, 116.32, 110.22, 63.27 (d,
JC–P =7.0 Hz), 63.07 (d, JC–P =6.8 Hz), 55.47, 53.95, 16.60
(dd, JC–P =20.9 Hz, 5.4 Hz). 31P NMR (162 MHz, DMSO)
δ 20.76. Anal. Calcd. for C23H22BrN2O5PS (%): C, 50.28; H,
4.04; N, 5.10 Found: C, 50.17; H, 3.91; N, 5.03.
1
IR (KBr,cm−1): 3418.48, 1716.49, 1543.33, 1233.39; H-
NMR (400 MHz, DMSO-d6) δ 8.72 (dd, J = 9.8, 3.4 Hz,
1H), 8.69 (s, 1H), 7.95 – 7.88 (m, 1H), 7.61 (ddd, J=8.6,
7.3, 1.6 Hz, 1H), 7.57 (s, 1H), 7.55 – 7.50 (m, 2H), 7.46 –
7.35 (m, 2H), 6.95 (d, J= 8.4 Hz, 2H), 5.65 (dd, J= 21.3,
9.7 Hz, 1H), 4.16 – 3.99 (m, 2H), 3.95 (ddt, J = 17.4,
14.3, 6.7 Hz, 1H), 3.89 – 3.76 (m, 1H), 3.74 (s, 3H), 1.19
(t, J = 7.0 Hz, 3H), 1.08 (t, J = 7.0 Hz, 3H). 13C NMR
(101 MHz, DMSO-d6) δ = 166.63 (d, JC–P = 11.4 Hz),
159.27, 159.24, 159.22, 152.69, 143.15, 138.97, 131.93,
130.06 (d, JC–P =5.9 Hz), 129.23, 125.12, 120.81, 119.86,
116.29, 114.06, 109.96, 62.96 (d, JC–P =6.9 Hz), 62.83 (d,
JC–P =6.8 Hz), 55.54, 55.31, 53.77, 16.76 (d, JC–P =5.2 Hz),
16.56 (d, JC–P =5.5 Hz). 31P NMR (162 MHz, DMSO-d6)
δ 21.78. Anal. Calcd. for C24H25N2O6PS (%): C, 57.59; H,
5.03; N, 5.60 Found: C, 57.65; H, 5.13; N, 5.67.
Diethyl((4‑chlorophenyl)((5‑(2‑oxo‑2H‑chromen‑3‑yl)thia‑
zol‑2‑yl)amino)methyl)phosphonate (IV)h White powder.
Recrystallized from EtOH. Yield: 75%; mp: 193.5–194.4 °C;
1
IR (KBr,cm−1): 3491.91, 1720.44, 1539.00, 1234.45; H-
NMR (400 MHz, DMSO-d6) δ 8.79 (dd, J = 9.6, 3.9 Hz,
1H), 8.66 (s, 1H), 7.88 (dd, J = 7.8, 1.6 Hz, 1H), 7.66 –
7.57 (m, 3H), 7.58 (s, 1H), 7.51 – 7.36 (m, 3H), 5.73 (dd,
J=22.0, 9.6 Hz, 1H), 4.15 – 4.00 (m, 2H), 4.00 – 3.82 (m,
D i e t h y l ( ( 4 ‑ ( d i m e t h y l a m i n o ) p h e n y l )
((5‑(2‑oxo‑2H‑chromen‑3‑yl)thiazol‑2‑yl)amino)methyl)
phosphonate (IV)k Brown powder. Recrystallized from
EtOH. Yield: 65%; mp: 207.1–208.3 °C; IR (KBr,cm−1):
2H), 1.19 (t, J=7.0 Hz, 3H), 1.10 (t, J=7.0 Hz, 3H). 13
C
1
NMR (101 MHz, DMSO-d6) δ=166.51 (d, JC–P =11.5 Hz),
164.76, 159.20, 152.70, 143.13, 139.06, 135.94, 132.85 (d,
JC–P = 3.2 Hz), 131.96, 131.82, 130.60 (d, JC–P = 5.8 Hz),
129.80, 129.19, 128.65 (d, JC–P = 2.1 Hz), 125.22 (d,
JC–P = 19.3 Hz), 120.78, 119.84, 116.30, 110.16, 63.22
(d, JC–P = 6.9 Hz), 63.02 (d, JC–P = 6.8 Hz), 55.42, 53.89,
16.73 (d, JC–P = 5.4 Hz), 16.53 (d, JC–P = 5.5 Hz).31P
NMR (162 MHz, DMSO-d6) δ 20.92. Anal. Calcd. for
C23H22ClN2O5PS (%): C, 54.71; H, 4.39; N, 5.55 Found: C,
54.79; H, 4.48; N, 5.61.
3422.00, 1723.21, 1541.27, 1216.59; H NMR (400 MHz,
DMSO-d6) δ=8.67 (s, 1H), 8.60 (dd, J=9.8, 3.2, 1H), 7.96
– 7.89 (m, 1H), 7.66 – 7.53 (m, 2H), 7.46 – 7.35 (m, 4H),
6.71 (d, J=8.4, 2H), 5.55 (dd, J=21.1, 9.7, 1H), 4.06 (ddd,
J = 16.6, 9.7, 6.9, 2H), 3.93 (dt, J = 10.2, 7.1, 1H), 3.87 –
3.72 (m, 1H), 3.33 (s, 1H), 2.87 (s, 6H), 1.18 (t, J = 7.0,
3H), 1.08 (t, J = 7.0, 3H). 13C NMR (101 MHz, DMSO-
d6) δ=166.74 (d, JC–P =11.5 Hz), 159.23, 152.68, 150.39,
143.15, 138.88, 131.92, 129.58 (d, JC–P =6.0 Hz), 129.26,
125.12, 123.64, 120.86, 119.87, 116.28, 112.37, 109.82,
62.77 (dd, JC–P = 9.7 Hz, 6.8 Hz), 55.44, 53.88, 16.78 (d,
JC–P =5.3 Hz), 16.60 (d, JC–P =5.5 Hz). 31P NMR (162 MHz,
DMSO) δ 22.12. Anal. Calcd. for C25H28N3O5PS (%): C,
58.47; H, 5.50; N, 8.18 Found: 58.54; H, 5.59; N, 8.25.
Diethyl(((5‑(2‑oxo‑2H‑chromen‑3‑yl)thiazol‑2‑yl)amino)
(3‑methoxyphenyl)methyl)phosphonate (IV)i Yellow powder.
Recrystallized from EtOH. Yield: 69%; mp: 228.9–229 °C;
1
IR (KBr,cm−1): 3419.59, 1719.13, 1539.12, 1247.39; H
NMR (400 MHz, DMSO-d6) δ = 8.75 (s, 1H), 8.70 (dd,
J = 9.8, 3.3, 1H), 7.83 – 7.91 (m, 1H), 7.56 – 7.66 (m,
2H), 7.35 – 7.46 (m, 2H), 6.97 (d, J= 1.9, 2H), 5.64 (dd,
J=21.2, 9.7, 1H), 3.81 – 4.18 (m, 4H), 3.31 (s, 3H), 1.21
(t, J=7.0, 3H), 1.10 (t, J=7.0, 3H). 13C NMR (101 MHz,
DMSO-d6) δ=166.61 (d, JC–P =11.3 Hz), 159.21, 153.04
(d, JC–P = 2.0 Hz), 152.72, 143.18, 139.06, 132.07 (d,
JC–P = 25.4 Hz), 129.04, 125.18, 120.83, 119.91, 116.33,
110.03, 106.65 (d, JC–P =5.9 Hz), 62.98 (t, JC–P =6.5 Hz),
60.46 (d, JC–P = 1.6 Hz), 56.48, 16.78 (d, JC–P = 5.3 Hz),
16.56 (d, JC–P = 5.6 Hz). 31P NMR (162 MHz, DMSO) δ
Diethyl(((5‑(2‑oxo‑2H‑chromen‑3‑yl)thiazol‑2‑yl)amino)
(1H‑pyrrol‑2‑yl)methyl)phosphonate (IV)l Red solid. Recrys-
tallized from EtOH. Yield: 91%; mp: 210.5–211.4 °C;
IR (KBr,cm−1): 3432.87, 1723.99, 1537.69, 1231.70;
1H NMR (400 MHz, DMSO-d6) δ = 10.75 (s, 1H), 8.71
(s, 1H), 8.40 (dd, J = 9.5, 2.0, 1H), 7.85 (dd, J = 7.7, 1.6,
1H), 7.62 (ddd, J = 8.7, 7.3, 1.6, 1H), 7.58 (s, 1H), 7.47
– 7.34 (m, 2H), 6.72 (dq, J = 2.6, 1.3, 1H), 6.21 (dq,
J = 4.0, 2.1, 1H), 6.01 (q, J = 2.8, 1H), 5.72 (dd, J = 20.5,
9.5, 1H), 4.16 – 3.75 (m, 3H), 1.18 (t, J= 7.0, 3H), 1.08
(t, J=7.1, 3H). 13C NMR (101 MHz, DMSO-d6) δ 166.72
1 3