Med Chem Res
(s, 1H), 8.90 (s, 1H). 13C NMR (300 MHz, CDCl3) d:
127.86(C-1), 140.93(C-2), 144.73(C-3), 154.17(C-4), 118.37
(C-5), 127.86(C-6), 157.05(C-7), 154.17(C0-1), 102.13(C0-2),
162.10(C0-3), 108.85(C0-4), 131.59(C0-5), 109.29(C0-6),
60.10(–OCH3), 57.07(R2–OCH3). MS (ESI): 303
(C15H15N2O5, [M?H]?). Anal. Calcd for C15H14N2O5: C,
59.60; H, 4.67; N, 9.27; Found: C, 59.49; H, 4.78; N, 9.08.
8.99 (s, 1H). 13C NMR (300 MHz, CDCl3) d: 127.36(C-1),
140.93(C-2), 144.75(C-3), 157.85(C-4), 118.70(C-5),
127.97(C-6), 157.85(C-7), 145.60(C0-1), 121.07(C0-2),
115.35(C0-3), 160.43(C0-4), 114.77(C0-5), 119.94(C0-6),
61.90(–OCH3), 56.53(R3–OCH3). MS (ESI): 303
(C15H15N2O5, [M?H]?). Anal. Calcd for C15H14N2O5: C,
59.60; H, 4.67; N, 9.27; Found: C, 59.39; H, 4.48; N, 9.13.
(E)-2-Methoxy-3-nitro-4-(((3-
(E)-2-Methoxy-3-nitro-4-(((4-
nitrophenyl)imino)methyl)phenol (4h)
nitrophenyl)imino)methyl)phenol (4l)
1
M.p. 151–152 °C. 1H NMR (300 MHz, CDCl3): 4.00 (s, 3H),
6.99 (s, 1H), 7.11–7.13 (m, 3H), 7.23–7.24 (m, 2H), 9.01 (s,
1H), 9.22 (s, 1H). 13C NMR (300 MHz, CDCl3) d: 126.01(C-
1), 142.13(C-2), 145.94(C-3), 156.05(C-4), 120.17(C-5),
126.01(C-6), 157.43(C-7), 154.58(C0-1), 112.12(C0-2),
149.55(C0-3), 121.89(C0-4), 131.71(C0-5), 122.35(C0-6),
59.90(–OCH3). MS (ESI): 318 (C14H12N3O6, [M?H]?).
Anal. Calcd for C14H11N3O6: C, 53.00; H, 3.49; N, 13.24;
Found: C, 52.89; H, 3.56; N, 13.09.
M.p. 143–145 °C. H NMR (300 MHz, CDCl3): 3.76 (s,
3H), 6.96–6.97 (d, J = 3.0 Hz, 1H), 7.23–7.24 (m, 3H),
7.68–7.71 (m, 2H), 9.12 (s, 1H), 9.62 (s, 1H). 13C NMR
(300 MHz, CDCl3) d: 127.82(C-1), 140.93(C-2), 145.94(C-
3), 156.15(C-4), 119.97(C-5), 130.07(C-6), 157.96(C-7),
166.33(C0-1), 118.30(C0-2), 124.54(C0-3), 145.87(C0-4),
124.96(C0-5), 118.98(C0-6), 61.50(–OCH3). MS (ESI): 318
(C14H12N3O6, [M?H]?). Anal. Calcd for C14H11N3O6: C,
53.00; H, 3.49; N, 13.24; Found: C, 53.11; H, 3.57; N, 13.33.
(E)-4-(((4-Bromophenyl)imino)methyl)-2-methoxy-3-
(E)-4-(((3,4-Dichlorophenyl)imino)methyl)-2-methoxy-3-
nitrophenol (4i)
nitrophenol (4m)
1
M.p. 153–155 °C. H NMR (300 MHz, CDCl3): 3.77 (m,
M.p. 95–96 °C. 1H NMR (300 MHz, CDCl3) : 3.71 (s, 3H),
6.96–6.97 (d, J = 3.0 Hz, 1H), 7.12–7.14 (m, 2H), 7.33–7.34
(d, J = 3.0 Hz, 1H), 7.72 (s, 1H), 8.79 (s, 1H), 8.86 (s, 1H).
13C NMR (300 MHz, CDCl3) d: 128.01(C-1), 140.93(C-2),
144.34(C-3), 155.05(C-4), 119.97(C-5), 127.82(C-6), 161.83
(C-7), 149.55(C0-1), 118.71(C0-2), 132.92(C0-3), 126.95
(C0-4), 132.15(C0-5), 121.52(C0-6), 61.50(–OCH3). MS (ESI):
350 (C14H11Cl2N2O4, [M?H]?). Anal. Calcd for C14H10
Cl2N2O4: C, 49.29;H, 2.95; N, 8.21; Found: C, 49.33;H, 2.78;
N, 8.36.
3H), 7.06 (s, 2H), 7.19–7.20 (m, 2H), 7.25–7.27 (m, 2H), 9.02
(s, 1H), 9.45 (s, 1H). 13C NMR (300 MHz, CDCl3) d:
127.45(C-1), 139.80(C-2), 144.94(C-3), 154.15(C-4), 118.71
(C-5), 128.97(C-6), 160.70(C-7), 152.68(C0-1), 120.85(C0-2),
132.70(C0-3), 118.03(C0-4), 131.59(C0-5), 122.88(C0-6),
61.83(–OCH3). MS (ESI): 350 (C14H12BrN2O4, [M?H]?).
Anal. Calcd for C14H11BrN2O4: C, 47.89; H, 3.16; N, 7.98;
Found: C, 47.95; H, 3.30; N, 7.72.
(E)-2-Methoxy-3-nitro-4-((p-tolylimino)methyl)phenol (4j)
(E)-4-(((2,4-d-Dichlorophenyl)imino)methyl)-2-methoxy-3-
M.p. 101–102 °C. 1H NMR (300 MHz, CDCl3): 2.80 (s, 3H),
3.81 (m, 3H), 7.19 (s, 1H), 7.35–7.36 (m, 2H), 7.55–7.57 (m,
2H), 7.66–7.67 (d, J = 3.0 Hz, 1H), 8.34 (s, 1H), 8.60 (s, 1H).
13C NMR (300 MHz, CDCl3) d: 127.82(C-1), 139.92(C-2),
145.04(C-3), 154.15(C-4), 118.75(C-5), 127.97(C-6), 154.15
(C-7), 152.67(C0-1), 118.34(C0-2), 130.41(C0-3), 134.11
(C0-4), 130.41(C0-5), 121.66(C0-6), 62.80(–OCH3), 19.05
(–CH3). MS (ESI): 287 (C15H15N2O4, [M?H]?). Anal. Calcd
for C15H14N2O4: C, 62.93; H, 4.93; N, 9.79; Found: C, 63.11;
H, 4.82; N, 9.57.
nitrophenol (4n)
M.p. 107–108 °C. 1H NMR (300 MHz, CDCl3): 3.82 (s, 3H),
6.77–6.78 (m, 2H), 7.19 (s, 1H), 7.55 (s, 1H), 7.68–7.71 (m,
1H), 9.12 (s, 1H), 9.45 (s, 1H). 13C NMR (300 MHz, CDCl3)
d: 127.45(C-1), 139.73(C-2), 145.94(C-3), 156.75(C-4),
118.91(C-5), 127.80(C-6), 160.06(C-7), 148.60(C0-1), 122.88
(C0-2), 130.41(C0-3), 131.65(C0-4), 130.69(C0-5), 121.67
(C0-6), 61.91(–OCH3). MS (ESI): 350 (C14H11Cl2N2O4,
[M?H]?). Anal. Calcdfor C14H10Cl2N2O4:C, 49.29;H, 2.95;
N, 8.21; Found: C, 49.41; H, 2.99; N, 8.09.
(E)-2-Methoxy-4-(((4-methoxyphenyl)imino)methyl)-3-
nitrophenol (4k)
(E)-4-(((2,5-Dichlorophenyl)imino)methyl)-2-methoxy-3-
nitrophenol (4o)
1
M.p. 104–105 °C. H NMR (300 MHz, CDCl3): 3.41 (s,
3H), 3.52 (m, 3H), 6.82–8.83 (d, J = 3.0 Hz, 1H), 6.99 (s,
1
M.p. 115–116 °C. H NMR (300 MHz, CDCl3): 4.00 (s,
3H), 6.86–6.87 (d, J = 3.0 Hz, 1H), 7.25–7.27 (m, 3H),
1H), 7.01–7.03 (m, 3H), 7.55–7.56 (m, 2H), 8.83 (s, 1H),
123