Medicinal Chemistry Research
J = 4.8 Hz, 1H), 7.41 (d, J = 4.8 Hz, 1H). 13C NMR
(100 MHz, DMSO-d6): 160.1, 152.5, 150.4, 135.3, 129.9,
124.6. IR (KBr, cm−1) 1627.1 (C=N), 1582.8, 1470.2,
1418.0. MS (ESI) m/z: 211.1 [M+H]+.
C6H4), 3.91 (t, 4H, 2 × CH2), 3.81 (s, 6H, 2 × OCH3). IR
(KBr, cm−1) 3440 (O-H), 2969, 2919 (C-H), 1641(C=N),
1604, 1509, 1457, 1308 (C-N), 1282, 1020 (C-O-C). 239.1
[M+H]+.
(1E,1’E)-N,N’-(ethane-1,2-diyl)bis(1-phenylmethanimine)
(1E,1’E)-N,N’-(ethane-1,2-diyl)bis(1-(pyridin-4-yl)methani-
mine) (4g) Yellow solid, 49.6% yield, 98.7% purity. H
NMR (400 MHz, CDCl3) δ 8.62 (s, 2H, 2 × CH = ),
8.42–7.29 (m, 8H, 2 × C6H4), 4.06(s, 4H, 2 × CH2). 13C
NMR (100 MHz, DMSO-d6): 163.5, 154.5, 149.8, 137.3,
125.5, 120.9. MS (ESI) m/z: 239.1 [M+H]+.
1
(4a) Bright
yellow
solid,
77.46%
yield,
mp
180.4–182.4 °C, 98.6% purity. 1H NMR (400 MHz, CDCl3)
δ 8.76 (dd, J1 = 3.6 Hz, J2 = 1.2 Hz, 4H), 8.58 (s, 2H), 7.71
(dd, J1 = 3.2 Hz, J2 = 1.2 Hz, 4H). 13C NMR (100 MHz,
DMSO-d6): 160.1, 151.0, 140.9, 122.5. IR (KBr, cm−1
)
1627.5 (C=N), 1594.5, 1551.7, 1417.5. MS (ESI) m/z:
237.1 [M+H]+.
2,2’-((1E,1’E)-((azanediylbis(ethane-2,1-diyl))bis(azanylyli-
dene))bis(methanylylidene))diphenol (5a) Yellow solid,
40.3% yield, 97.6% purity. H NMR (400 MHz, CDCl3) δ
1
2,2’-((1E,1’E)-(ethane-1,2-diylbis(azanylylidene))bis(metha-
nylylidene))diphenol (4b) Bright yellow solid, 70.4%
yield, 98.3% purity. 1H NMR (400 MHz, CDCl3) δ 8.29 (s,
2H, 2 =CH), 7.70–7.68 (m, 4H, C6H5), 7.40–7.36 (m, 4H,
C6H5), 3.98 (s, 4H, 2 × CH2). 13C NMR (100 MHz, DMSO-
d6): 161.6, 129.9, 129.4, 114.5, 61.5, 55.7. MS (ESI) m/z:
269.1 [M+H]+.
8.83(s, 2 H, 2 × CH = ), 8.64–7.33 (m, 8H, 2 × C6H4), 4.02
(s, 4H, 2 × CH2). MS (ESI) m/z: 312.2 [M+H]+.
4,4’-((1E,1’E)-((azanediylbis(ethane-2,1-diyl))bis(azanylyli-
dene))bis(methanylylidene))bis(2-methoxyphenol) (5b)
Yellow solid, 36.8% yield, 97.8% purity. 1H NMR
(400 MHz, CDCl3) δ 8.67–8.69 (m, 4H, 2 × CH =+C6H4),
8.29 (t, 2H, C6H4), 7.58–7.55 (m, 4H, C6H4), 4.06 (q, 4H,
2 × CH2). 13C NMR (100 MHz, DMSO-d6): 161.4, 150.8,
143.0, 122.2, 61.0. MS (ESI) m/z: 372.2 [M+H]+.
4,4’-((1E,1’E)-(ethane-1,2-diylbis(azanylylidene))bis(metha-
nylylidene))bis(2-methoxyphenol) (4c) Bright yellow
solid, 68.8% yield, mp 124.5–125.0 °C, 97.8% purity. H
1
NMR (400 MHz, CDCl3)δ 13.23 (s, 2H, 2 × OH), 8.36 (s,
2H, 2 × CH = ), 7.23–7.30 (m, 4H, C6H4), 6.86–6.95 (m,
4H, C6H4), 3.94 (s, 4H, 2 × CH2). 13C NMR (100 MHz,
DMSO-d6): 167.4, 161.0, 132.8, 132.1, 119.1, 119.0, 116.9,
59.2. IR (KBr, cm−1) 3438 (O-H), 2928 (C-H), 1634
(C=N), 1578, 1497, 1459, 1416, 1284 (C-N), 1202, 1194
(C-O-C). MS (ESI) m/z: 329.1 [M+H]+.
2,2’-((1E,1’E)-(((2-(2-hydroxyphenyl)imidazolidine-1,3-diyl)
bis(ethane-2,1-diyl))bis(azanylylidene))bis(methanylyli-
dene))diphenol (6a) Bright yellow solid, 33.02% yield,
1
97.6% purity. H NMR (400 MHz, CDCl3) δ 13.12–13.27
(m, 1H, OH), 8.25 (s, 1H, CH = ), 6.79–7.31 (m, 9H, 2 ×
C6H4, CH = ), 3.42–3.83 (m, 5H, 2 × CH2+OH), 2.95~2.98
(m, 1H, NH), 2.66–2.69 (m, 4H, 2 × CH2). IR (KBr, cm−1
)
(1E,1’E)-N,N’-(ethane-1,2-diyl)bis(1-(2-bromophenyl)metha-
nimine) (4d) Bright yellow solid, 60.21% yield, 98.0%
purity. 1H NMR (400 MHz, DMSO) δ 9.54 (s, 2H, 2 × OH),
8.19 (s, 2H, 2 × CH = ), 7.32–6.70 (m, 6H, 2 × C6H3), 3.78
(s, 10H, 2 × CH2+2 × OCH3). 13C NMR (100 MHz,
DMSO-d6): 161.9, 148.3, 128.4, 128.4, 123.1, 115.7,
110.40, 61.4, 55.9. MS (ESI) m/z: 393.0 [M+H]+.
3427(O-H), 2860, 2822(C-H), 1631(-CH=N), 1580, 1495,
1456, 1414.9, 1261(C-N), 1206, 1116 (C-O-C). MS (ESI)
m/z: 459.2 [M+H]+.
4,4’-((1E,1’E)-(((2-(4-hydroxy-3-methoxyphenyl)imidazoli-
dine-1,3-diyl)bis(ethane-2,1-diyl))bis(azanylylidene))bis
(methanylylidene))bis(2-methoxyphenol)
(6b) Yellow
1
solid, 68.48% yield, mp 103.2–104.0 °C, 97.7% purity. H
NMR (400 MHz, CDCl3) δ 13.24 (s, 2H), 10.70 (s, 1H), 8.25
(s, 2H), 7.29 (dt, J1 = 6.8 Hz, J2 = 2.0 Hz, 2H), 7.25 (dd,
J1 = 6.4 Hz, J2 = 0.8 Hz, 1H), 7.21 (dd, J1 = 6.0 Hz, J2 =
1.6 Hz, 2H), 7.00 (dd, J1 = 6.0 Hz, J2 = 1.6 Hz, 1H), 6.93 (d,
J = 8.0 Hz, 2H), 6.86 (dt, J1 = 6.8 Hz, J2 = 0.8 Hz, 2H), 6.82
(dd, J1 = 3.6 Hz, J2 = 0.8 Hz, 1H), 6.82 (dd, J1 = 3.6 Hz,
J2 = 0.8 Hz, 1H), 6.80 (dd, J1 = 4.4 Hz, J2 = 0.8 Hz, 1H),
3.83 (s, 1H), 3.60 (t, J = 6.4 Hz, 4H), 3.45–3.41 (m, 2H),
2.99 (t, J = 6.4 Hz, 1H), 2.95 (t, J = 6.4 Hz, 1H), 2.71–2.62
(m, 4H). IR (KBr, cm−1) 3439 (O-H), 2856、2802 (C-H),
1632 (C=N), 1581, 1494, 1460, 1415, 1372, 1312(C-N),
1206, 1033 (C-O-C). MS (ESI) m/z: 549.3 [M+H]+.
(1E,1’E)-N,N’-(ethane-1,2-diyl)bis(1-(4-methoxyphenyl)
methanimine) (4e) Bright yellow solid, 56.27% yield,
1
98.3% purity. H NMR (400 MHz, CDCl3) δ 8.65 (s, 2H,
2 × CH = ), 8.0–7.23 (m, 8H, 2 × C6H4), 4.03(s, 4H, 2 ×
CH2). 13C NMR (100 MHz, DMSO-d6): 161.1, 134.5,
133.5, 132.9, 129.0, 128.4, 124.6, 60.9. MS (ESI) m/z:
297.2 [M+H]+.
(1E,1’E)-N,N’-(ethane-1,2-diyl)bis(1-(pyridin-2-yl)methani-
mine) (4f) Yellow solid, 62% yield, mp 153.2–153.5 °C,
1
98.5% purity. H NMR (400 MHz, CDCl3)δ 8.20 (s, 2H,
2 × CH = ), 7.64–7.62 (m, 4H, C6H4), 6.90–6.88 (m, 4H,