1960 Jiang
Asian J. Chem.
R
N
NH
O
O
O
R
(1) SOCl2
NH
N
N
HN
OH
O
2
NH2
N
OH
NH2
OH
(2)
OH HO
HO
1
3a- 3g
H3CO
Cl
Cl
R= 3a:
3e:
CH3
3b:
3c:
3g:
3d:
NO2
3f:
CN
Structure of compounds 3a-3g
2,2'-(6-((2-Methoxyphenyl)amino)-1,3,5-triazine-2,4-
diyl)diphenol (3b): The title compound was synthesized from
1-(2-methoxyphenyl)guanidine hydrochloride (2.01 g, 0.01
mol), refluxed for 3 h, yellow powder; yield 3.25 g (84.17 %);
m.p.: 191-192 °C; 1H NMR (DMSO-d6) δ: 12.84 (s, 1H, OH),
12.60 (s, 1H, OH), 10.51 (s, 1H, NH), 8.44 (d, J = 7.0 Hz, 1H,
ArH), 8,33 (d, J = 7.5 Hz, 1H, ArH), 7.53-6.87 (m, 10H, ArH),
3.82 (s, 3H, OCH3). IR: (KBr, νmax, cm-1): 3428, 3322, 1253, 1029.
2,2'-(6-((2-Chlorophenyl)amino)-1,3,5-triazine-2,4-
diyl)diphenol (3c): The title compound was synthesized from
1-(2-chlorophenyl)guanidine hydrochloride (2.05 g, 0.01 mol),
refluxed for 5 h, yellow powder; yield 2.7 g (69.23 %); m.p.:
190-192 °C; 1H NMR (DMSO-d6) δ: 12.84 (s, 1H, OH), 12.45
(s, 1H, OH), 10.84 (s, 1H, NH), 8.46-8.43 (m, 2H,ArH), 7.71-
δ: 14.12 (s, 1H, OH), 13.80 (s, 1H, OH), 12.65 (s, 1H, NH),
8,44-8.40 (m, 2H, ArH), 7.59-6.93 (m, 8H, ArH). IR: (KBr,
ν
max, cm-1): 3421, 2175.
Reaction of substituted guanidine and 2-(2-hydroxy-
phenyl)-4H-benzo[e][1,3]oxazin-4-one afforded novel o-hydroxy-
phenyl-substituted 1,3,5-triazine in good to high yields. The
structures of the products were confirmed by IR, ESI-MS, 1H
NMR spectral methoda. For example, the 1H NMR spectrum
of compound 4 shows two singlets at δ 12.84 and 12.45 but
the compound 5 shows one singlet at δ 12.55 for symmetrical
structure.
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2,2'-(6-((4-Chlorophenyl)amino)-1,3,5-triazine-2,4-
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1
215-217 °C; H NMR (DMSO-d6) δ: 12.55 (s, 2H, 2-OH),
10.88 (s, 1H, NH), 8.41 (d, J = 7.65 Hz, 2H), 7.58-7.06 (m,
10H, ArH). IR: (KBr, νmax, cm-1): 3296, 755.
2,2'-(6-((4-Nitrophenyl)amino)-1,3,5-triazine-2,4-
diyl)diphenol (3e): The title compound was synthesized from
1-(4-nitrophenyl)guanidine hydrochloride (2.16 g, 0.01 mol),
refluxed for 6 h, yellow powder; yield 3.22 g (80.3 %); m.p.:
1
279-281 °C; H NMR (DMSO-d6) δ: 12.95 (s, 2H, 2-OH),
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11.37 (s, 1H, NH), 8.38 (d, J = 9.15 Hz, 2H, ArH), 8.07-7.05
(m, 10H, ArH). IR: (KBr, νmax, cm-1): 3446, 3329, 1534, 1333.
2,2'-(6-(Benzylamino)-1,3,5-triazine-2,4-diyl)diphenol
(3f)The title compound was synthesized from 1-benzylguanidine
hydrochloride (1.85 g, 0.01 mol), refluxed for 6 h, yellow
powder; yield 2.56 g (69.19 %); m.p.: 194-196 °C; 1H NMR
(DMSO-d6) δ: 13.16 (s, 1H, OH), 12.87 (s, 1H, OH), 9.48 (t, J
= 5.95 Hz, 1H, NH), 8.31-7.01 (m, 13H, ArH), 4.66 (d, J =
5.95 Hz, 2H, CH2). IR: (KBr, νmax, cm-1): 3392, 3335.
N-(4,6-bis(2-Hydroxyphenyl)-1,3,5-triazin-2-yl)cyana-
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amide (0.84 g, 0.01 mol) and sodium hydroxide (0.05 g, 1.25
mmol), refluxed for 3 h, pale yellow powder; yield 2.78 g
(91.15 %); m.p.: 250 °C; (decomposition). 1H NMR (DMSO-d6)
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