5364
D. M. Boghaei, S. Mohebi / Tetrahedron 58 .2002) 5357±5366
properties, spectral data and other characterization data are
given below.
10.67 <s, 2H, O±H), 6.25±7.59 <m, 10H, H-aryl), 2.33
<s, 6H, CH3<azomethine)). 13C NMR <500 MHz) chemical shift
<d ppm) 19, 103 <2), 107, 108, 113, 115 <2), 118 <2), 122,
126, 133 <3), 141, 162, 173.
4.3.1. Compound 1. F.W.330.39, yield 71%, color
yellow-orange, mp148.1±149.78C. Selective IR bands
<cm21), KBr pellets <O±H, CvN, C±O), 3400, 1623 <w),
1246. Anal. calcd for C21H18N2O2: C, 76.23; H, 5.49; N,
8.48. Found: C, 76.17; H, 5.65; N, 8.58. 1H NMR
<500 MHz) chemical shift <d ppm), 13.65 <br, 2H, O±H),
8.16 <s, 1H, CHvN), 6.48±7.61 <m, 12H, H-aryl), 2.21 <s,
3H, CH3<azomethine)). 13C NMR <500 MHz) chemical shift <d
ppm) 18, 118, 119, 120 <3), 122, 125, 127, 128, 132 <3), 140,
142, 161, 162, 163, 172.
4.3.7. Compound 7. F.W.380.96, yield 37%, color red-
brown, mp1608C <decomposed). Selective IR bands
<cm21), KBr pellets <O±H, CvN, C±O), 3330, 1605 <w),
1223, 1240. Anal. calcd for C25H20N2O2: C, 78.82; H, 5.29;
N, 7.35. Found: C, 78.57; H, 5.01; N, 7.53. 1H NMR
<500 MHz) chemical shift <d ppm), 14.47 <s, 1H, O±H),
12.83 <s, 1H, O±H), 8.57 <s, 1H, CHvN), 6.50±7.45 <m,
14H, H-aromatic), 2.25 <s, 3H, CH3<azomethine)). 13C NMR
<500 MHz) chemical shift <d ppm) 57, 113 <2), 116 <2),
118, 119, 127 <2), 129 <2), 132, 133, 135, 136, 143, 144,
153, 155, 162, 164.
4.3.2. Compound 2. F.W.346.39, yield 59%, color red-
brown. mp1258C <decomposed). Selective IR bands
<cm21), KBr pellets <O±H, CvN, C±O), 3330, 3180,
1623 <w), 1276. Anal. calcd for C21H18N2O3: C, 72.82;
4.3.8. Compound 8. F.W.396.45, yield 21%, color red-
brown, mp1608C <decomposed), Selective IR bands
<cm21), KBr pellets <O±H, CvN, C±O), 3365, 3315,
1600 <w), 1246. Anal. calcd for C25H20N2O3: C, 75.74; H,
1
H5.24; N, 8.09. Found: C, 72.93; H, 5.29; N, 8.17. H
NMR <500 MHz) chemical shift <d ppm), 12.65 <br, 2H,
O±H), 6.1 <br, 1H, O±H), 8.68 <s, 1H, CHvN), 2.12 <s,
3H, CH3<azomethine)), 6.50±7.53 <m, 11H, H-aryl). 13C NMR
<500 MHz) chemical shift <d ppm) 19, 103 <2), 107, 108,
113, 115 <2), 117 <3), 120, 122, 125, 127 <3), 132, 134 <2),
141, 142, 161, 164, 165, 173.
1
5.08; N, 7.07. Found: C, 75.60; H, 4.96; N, 7.26. H NMR
<500 MHz) chemical shift <d ppm), 14.73 <s, 1H, O±H),
12.68 <s, 1H, O±H), 9.71 <s, 1H, CHvN), 6.51±7.55
<m, 13H, H-aromatic), 5.74 <s, 1H, O±H), 2.61 <s, 3H,
CH3<azomethine)). 13C NMR <500 MHz) chemical shift <d
ppm) 61, 105, 108 <2), 113 <2), 116 <2), 127 <2), 129 <2),
132, 135, 136, 144, 153, 156, 163, 165.
4.3.3. Compound 3. F.W.360.41, yield 31%, color red-
brown. mp1138C <decomposed). Selective IR bands
<cm21) KBr pellets, <O±H, CvN, C±O), 3359, 1623 <w),
1253. Anal. calcd for C22H20N2O3: C, 73.32; H, 5.59; N,
7.77. Found: C, 73.06; H, 5.65; N, 7.97. 1H NMR
<500 MHz) chemical shift <d ppm), 14.35 <br, 1H, O±H),
12.7 <br, 1H, O±H), 6.42±7.71 <m, 11H, H-aryl), 6.1 <br,
1H, O±H), 2.45 <s, 3H, CH3<azomethine)), 2.25 <s, 3H, CH3<azo-
4.3.9. Compound 9. F.W.410.47, yield 18%, color dark
brown, mp1708C <decomposed). Selective IR bands
<cm21), KBr pellets <O±H, CvN, C±O), 2976, 3373,
1607 <w), 1276. Anal. calcd for C26H22N2O3: C, 76.08; H,
1
5.40; N, 6.82. Found: C, 75.79; H, 5.11; N, 6.99. H NMR
13C NMR <500 MHz) chemical shift <d ppm), 18, 19,
<500 MHz) chemical shift <d ppm), 12.74 <s, 2H, O±H),
6.55±7.28 <m, 13H, H-aromatic), 5.82 <s, 1H, O±H), 2.58
<s, 3H, CH3<azomethine)), 2.21 <s, 3H, CH3<azomethine)). 13C NMR
<500 MHz) chemical shift <d ppm) 58, 61, 105, 108 <2), 113
<2), 116 <2), 119, 127 <2), 129 <2), 132, 135, 136, 144, 147,
154, 156, 163, 165.
methine)).
103 <2), 107, 108, 113, 115 <2), 118 <2), 120, 122, 126, 132
<3), 134, 140, 141, 162, 164, 172, 174.
4.3.4. Compound 4. F.W.316.36, yield 93%, color
orange, mp162.5±164.18C. Selective IR bands <cm21),
KBr pellets <O±H, CvN, C±O), 3415, 1615 <s), 1276.
Anal. calcd for C20H16N2O2: C, 75.93; H, 5.10; N, 8.85.
4.3.10. Compound 10. F.W.366.42, yield 46%, color
green, mp1608C <decomposed). Selective IR bands
<cm21), KBr pellets, <O±H, CvN, C±O), 3361, 1600 <s),
1246. Anal. calcd for C24H18N2O2: C, 78.67; H, 4.95; N,
7.64. Found: C, 78.48; H, 4.89; N, 7.91. 1H NMR
<500 MHz) chemical shift <d ppm), 14.82 <s, 2H, O±H),
9.58 <s, 2H, CHvN), 6.48±8.15 <m, 14H, H-aromatic).
13C NMR <500 MHz) chemical shift <d ppm) 113 <2), 116
<2), 118 <2), 121, 127 <2), 128, 129 <2), 135 <3), 144, 162,
155.
1
Found: C, 75.71; H, 5.01; N, 8.98. H NMR <500 MHz)
chemical shift <d ppm), 12.95 <s, 2H, O±H), 8.49 <s, 2H,
CHvN), 6.60±7.33 <m, 12H, H-aryl).
4.3.5. Compound 5. F.W.344.414, yield 45%, color
yellow-orange, mp81.9±83.58C. Selective IR bands
<cm21), KBr pellets <O±H, CvN, C±O), 3607, 1615 <s),
1276. Anal. calcd for C22H20N2O2: C, 76.72; H, 5.85; N,
8.13. Found: C, 76.54; H, 5.57; N, 8.32. 1H NMR
<500 MHz) chemical shift <d ppm), 14.85 <s, 2H, O±H),
6.31±7.83 <m, 12H, H-aryl), 2.25 <s, 6H, CH3<azomethine)).
13C NMR <500 MHz) chemical shift <d ppm) 18, 115 <2),
117, 118 <3), 120, 122, 126, 130, 132, 133, 135, 140, 162,
174.
4.3.11. Compound 11. F.W.394.47, yield 28%, color red-
brown, mp1808C <decomposed). Selective IR bands
<cm21), KBr pellets, 3338, 1605 <s), 1223. Anal. Calcd for
C26H22N2O2: C, 79.17; H, 5.62; N, 7.10. Found: C, 78.84; H,
5.55; N, 7.23. 1H NMR <500 MHz) chemical shift <d ppm),
12.75 <s, 2H, O±H), 6.48±7.62 <m, 14H, H-aromatic), 2.27
<s, 6H, CH3<azomethine)). 13C NMR <500 MHz) chemical shift
<d ppm) 57, 113 <2), 116 <2), 127 <2), 129 <2), 135, 136, 143,
144, 153, 163.
4.3.6. Compound 6. F.W.376.41, yield 25%, color brown,
mp1008C <decomposed). Selective IR bands <cm21), KBr
pellets<O±H, CvN, C±O), 3450, 3600, 1630 <s), 1276,
1207. Anal. calcd for C22H20N2O4: C, 70.20; H, 5.36; N,
7.44. Found: C, 70.01; H, 5.30; N, 7.64. 1H NMR
<500 MHz) chemical shift <d ppm), 12.56 <s, 2H, O±H),
4.3.12. Compound 12. F.W.426.47, yield 15%, color