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SOLVENT-FREE SYNTHESES OF SALICYLALDIMINES
2-[[(3-Benzyloxypyridine-2-yl)imino]methyl]-phenol
2399
(3l):
M.p.
106–107ꢀC; IR (KBr pellet) 3436.8, 1605.3, 1580.3, 1555.6, 1453.9, 1434.8,
1382.4, 1287.8, 1212.8, 1119.5, 1021.1, 762.3 cmÀ1; 1H NMR (CDCl3) ꢀ 5.21
(s, 2H), 6.79–7.48 (m, 11H), 8.10 (d, 1H), 9.44 (s, 1H), 14.17 (s, 1H) ppm;
13C NMR (CDCl3) ꢀ 70.3, 117.4, 118.3, 118.7, 119.1, 121.1, 126.7, 127.9,
128.5, 133.0, 133.6, 135.9, 139.9, 147.4, 148.5, 162.4, 162.9 ppm; Anal. calcd.
for C19H16N2O2: C, 74.98%; H, 5.30%; N, 9.20%; Found: C, 74.97%;
H, 5.33%; N, 9.17%.
2-[[(Acridine-9-yl)imino]methyl]-phenol (3m): M.p. 231–233ꢀC; IR (KBr
pellet) 3442.7, 2925.8, 1622.3, 1554.0, 1516.6, 1462.1, 1277.5, 1065.9,
1
753.5 cmÀ1; H NMR (CDCl3) ꢀ 7.05–8.26 (m, 12H), 8.64 (s, 1H), 12.43
(s, 1H) ppm; 13C NMR (CDCl3) ꢀ 116.4, 116.7, 117.2, 118.4, 122.2, 124.5,
128.3, 129.2, 131.9, 133.4, 148.0, 150.4, 160.0, 167.9 ppm; Anal. calcd. for
C20H14N2O: C, 80.52%; H, 4.73%; N, 9.39%; Found: C, 80.46%; H,
4.69%; N, 9.42%.
2-[[(4-Methylbenzothiazole-2-yl)imino]methyl]-phenol
99.5–102ꢀC; IR (KBr pellet) 3440.2, 2971.9, 1617.5, 1597.9, 1566.5,
1473.1, 1280.7, 1148.9, 752.2 cmÀ1 1H NMR (CDCl3) ꢀ 2.75 (s, 3H),
(3n):
M.p.
;
7.04–7.70 (m, 7H), 9.27 (s, 1H), 12.29 (s, 1H) ppm; 13C NMR (CDCl3) ꢀ
18.4, 117.6, 118.3, 119.0, 119.6, 125.1, 127.1, 133.2, 133.9, 134.4, 135.1,
150.8, 161.8, 167.1, 167.7 ppm; Anal. calcd. for C15H12N2OS: C, 67.14%;
H, 4.51%; N, 10.44%; Found: C, 67.16%; H, 4.50%; N, 10.39%.
2-[[(6-Ethylpyridine-2-yl)imino]methyl]-phenol (3o): M.p. 38.5–40ꢀC; IR
(KBr pellet) 3436.9, 2971.6, 1612.8, 1554.8, 1496.5, 1458.8, 1281.5, 1188.9,
1
815.5, 754.9 cmÀ1; H NMR (CDCl3) ꢀ 1.35 (t, 3H), 2.85 (q, 2H), 6.86–7.71
(m, 7H), 9.46 (s, 1H), 13.62 (s, 1H) ppm; 13C NMR (CDCl3) ꢀ 13.6, 31.1,
117.0, 117.3, 118.9, 120.8, 133.2, 133.4, 138.4, 156.6, 161.7, 163.0, 164.1,
172.2 ppm; Anal. calcd. for C14H14N2O: C, 74.31%; H, 6.24%; N,
12.38%; Found: C, 74.36%; H, 6.22%; N, 12.34%.
2-[[(4-Ethylpyridine-2-yl)imino]methyl]-phenol (3p): M.p. 46–48ꢀC; IR
(KBr pellet) 3433.1, 2969.0, 1601.9, 1575.9, 1545.9, 1455.6, 1411.0, 1280.1,
1147.2, 758.1 cmÀ1; 1H NMR (CDCl3) ꢀ 1.29 (t, 3H), 2.68 (q, 2H), 6.93–7.51
(m, 6H), 8.38 (d, 1H), 9.43 (s, 1H), 13.52 (s, 1H) ppm; 13C NMR (CDCl3) ꢀ
14.1, 28.0, 117.4, 119.0, 119.8, 121.9, 122.3, 133.2, 133.5, 148.5, 155.7, 157.5,
161.7, 164.3 ppm; Anal. calcd. for C14H14N2O: C, 74.31%; H, 6.24%; N,
12.38%; Found: C, 74.35%; H, 6.21%; N, 12.39%.
2-[[(3,5-Dibromo-6-methylpyridine-2-yl)imino]methyl]-phenol (3q): M.p.
149–150.5ꢀC; IR (KBr pellet) 3442.8, 1607.1, 1574.8, 1533.7, 1448.9,
1419.7, 1280.3, 1184.7, 1054.2, 757.7 cmÀ1 1H NMR (CDCl3) ꢀ 2.63
;
(s, 3H), 6.93–7.56 (m, 4H), 8.09 (s, 1H), 9.43 (s, 1H), 13.43 (s, 1H)
ppm; 13C NMR (CDCl3) ꢀ 24.3, 114.8, 117.5, 118.7, 118.9, 119.2,
133.7, 134.4, 144.1, 152.5, 155.5, 162.1, 165.2 ppm; Anal. calcd. for