Vol. 26, No. 12, 2015
Grasel et al.
2499
1
1241 ν(Ar-O), 1194 ν(C−N); H NMR (300 MHz,
DMSO-d6) d 11.09 (s, 1H, OH), 10.90 (s, 1H, NH), 8.41
(d, 1H, J 2.7 Hz, phenolic-H), 7.62-7.58 (m, 2H, Ar-H),
7.60 (dd, 1H, J 9.0, 2.7 Hz, phenolic-H), 7.57-7.52 (m,
2H, Ar-H), 7.13 (d, 1H, J 9.0 Hz, phenolic-H); 13C NMR
(75.4 MHz, DMSO-d6) d 169.9 (C2), 168.9 (C5’a), 163.9
(C5’b or C5’c), 153.8 (C2’), 151.3 (C9), 134.8 (C5’), 129.0 (C8),
127.4 (C5 or C6), 126.7 (C5 or C6), 124.8 (C4), 122.2 (C7 or
C4’), 122.0 (C4’ or C7), 119.8 (C6’), 118.2 (C1’), 117.3 (C3’);
HRMS (MALDI) m/z, calcd. for C16H9Cl2N5O2 [M + H]+:
388.9903; found: 388.9897.
596.0755; HRMS (ESI) m/z, calcd. for C29H18ClN7O2S2
[M – H]-: 594.0573; found: 594.0546.
2,4-Di[2-(5’-aminyl-2’-hydroxphenyl)benzothiazole]-6-
chloro-1,3,5-triazine (4d)
Yield 70%; beige solid; mp: decomposed before
melting; IR (nujol) νmax / cm-1: 3442 ν(OH), 3334 ν(NH),
1605 v(C=N), 1577 and 1502 νarom(C=C), 1260 ν(Ar-O),
1185 ν(C−N); 1H NMR (300 MHz, DMSO-d6) d 8.16 (d,
2H, J 1.8 Hz, 2phenolic-H); 8.01-7.85 (m, 4H, 2Ar-H);
7.58 (br, 2H, 2phenolic-H); 7.43-7.26 (m, 4H, 2Ar-H);
6.68 (br, 2H, 2phenolic-H); HRMS (ESI) m/z, calcd. for
C29H18ClN7O2S2 [M + H]+: 596.0730; found: 596.0732;
HRMS (ESI) m/z, calcd. for C29H18ClN7O2S2 [M – H]-:
594.0573; found: 594.0572.
2,4-Di[2-(4’-aminyl-2’-hydroxphenyl)benzoxazole]-6-chloro-
1,3,5-triazine (4a)
Yield 80%; white solid; mp: decomposed before
melting; IR (nujol) νmax / cm-1: 3454 ν(OH), 3295
ν(NH), 1619 ν(C=N), 1535, 1498 and 1451 νarom(C=C),
2,4,6-Tri[2-(4’-aminyl-2’-hydroxphenyl)benzoxazole]-1,3,5-
triazine (5a)
1
1236 ν(Ar-O), 1180 ν(C−N); H NMR (300 MHz,
DMSO-d6) d 11.46 (s, 2H, 2OH), 10.94 (s, 2H, 2NH),
8.08 (d, 2H, J 8.4 Hz, 2phenolic-H), 7.75 (d, 2H, J 1.8 Hz,
2phenolic-H), 7.72-7.60 (m, 4H, 2Ar-H), 7.44-7.37 (m, 4H,
2Ar-H), 7.14 (dd, 2H, J 8.4, 1.8 Hz, 2phenolic-H); HRMS
(ESI) m/z, calcd. for C29H18ClN7O4 [M + H]+: 564.1187;
found: 564.1191; HRMS (ESI) m/z, calcd. for C29H18ClN7O4
[M – H]-: 562.1030; found: 562.1020.
Yield 75%; white solid; mp: decomposed before
melting; IR (nujol) νmax / cm-1: 3494 ν(OH), 3379 ν(NH),
1641 ν(C=N), 1467 and 1388 νarom(C=C), 1246 ν(Ar-O),
1188 ν(C−N); 1H NMR (300 MHz, DMSO-d6) d 11.63 (s,
3H, 3OH), 7.68 (m, 6H, 3Ar-H and 3H, 3phenolic-H), 7.34
(m, 6H, 3Ar-H), 6.28 (dd, 3H, J 8.8, 2.3 Hz, 3phenolic-H),
6.18 (d, 3H, J 2.3, 3phenolic-H), 6.10 (s, 3H, 3NH); HRMS
(ESI) m/z, calcd. for C16H9Cl2N5O2 [M + H]+: 754.2163;
found: 754.2197; HRMS (ESI) m/z, calcd. for C16H9Cl2N5O2
[M – H]-: 752.2006; found: 752.2026.
2,4-Di[2-(5’-aminyl-2’-hydroxphenyl)benzoxazole]-6-chloro-
1,3,5-triazine (4b)
Yield 80%; white solid; mp: decomposed before
melting; IR (nujol) νmax / cm-1: 3418 ν(OH), 3330
ν(NH), 1616 ν(C=N), 1568, 1524 and 1498 νarom(C=C),
2,4,6-Tri[2-(5’-aminyl-2’-hydroxphenyl)benzoxazole]-1,3,5-
triazine (5b)
1
1235 ν(Ar-O), 1173 ν(C−N); H NMR (300 MHz,
Yield 80%; white solid; mp: decomposed before
melting; IR (nujol) νmax / cm-1: 3457 ν(OH), 3291
ν(NH), 1616 ν(C=N), 1568, 1533 and 1498 νarom(C=C),
DMSO-d6) d 10.59 (s, 2H, 2OH), 10.40 (s, 2H, 2NH), 8.62
(s, 2H, 2phenolic-H), 7.54-7.47 (m, 4H, 2Ar-H), 7.36 (d,
2H, J 8.1 Hz, 2phenolic-H), 7.16-7.28 (m, 4H, 2Ar-H), 7.04
(d, 2H, J 8.1 Hz, 2phenolic-H); HRMS (ESI) m/z, calcd.
for C29H18ClN7O4 [M + H]+: 564.1187; found: 564.1207;
HRMS (ESI) m/z, calcd. for C29H18ClN7O4 [M – H]-:
562.1030; found: 562.1041.
1
1226 ν(Ar-O), 1173 ν(C−N); H NMR (300 MHz,
DMSO-d6) d 11.18 (s, 3H, 3OH), 10.43 (s, 3H, 3NH),
8.62 (d, 3H, J 2.1 Hz, 3phenolic-H), 7.55 (dd, 3H, J 8.7,
2.1 Hz, 3phenolic-H), 7.48 (m, 6H, 3Ar-H), 7.37-7.23 (m,
6H, 3Ar-H), 7.05 (d, 3H, J 8.7 Hz, 3phenolic-H); HRMS
(ESI) m/z, calcd. for C42H27N9O6 [M + H]+: 754.2163;
found: 754.2174; HRMS (ESI) m/z, calcd. for C42H27N9O6
[M – H]-: 752.2006; found: 752.2028.
2,4-Di[2-(4’-aminyl-2’-hydroxphenyl)benzothiazole]-6-
chloro-1,3,5-triazine (4c)
Yield 75%; light green solid; mp: decomposed before
melting; IR (nujol) νmax / cm-1: 3454 ν(OH), 3333 ν(NH),
1609 ν(C=N), 1544 and 1460 νarom(C=C), 1236 ν(Ar-O),
2,4,6-Tri[2-(4’-aminyl-2’-hydroxphenyl)benzothiazole]-1,3,5-
triazine (5c)
1
1180 ν(C−N); H NMR (300 MHz, DMSO-d6) d 11.05
Yield 80%; beige solid; mp: decomposed before
melting; IR (nujol) νmax / cm-1: 3464 v(OH), 3370 ν(NH),
1619 ν(C=N), 1465 and 1371 νarom(C=C), 1193 ν(Ar-O),
1141 ν(C−N); 1H NMR (300 MHz, DMSO-d6) d 11.19 (s,
3H, 3OH), 8.03-7.86 (m, 6H, 3Ar-H), 7.62 (d, 3H, J 8.8 Hz,
3phenolic-H), 7.48-7.30 (m, 6H, 3Ar-H), 6.25-6.22 (dd,
(s, 2H, 2OH), 10.73 (s, 2H, 2NH), 8.26 (d, 2H, J 8.4,
2phenolic-H), 8.19-7.97 (m, 4H, 2Ar-H), 7.72 (d, 2H,
J 1.8 Hz, 2phenolic-H), 7.57-6.93 (m, 4H, 2Ar-H), 7.09
(dd, 2H, J 8.4, 1.8 Hz, 2phenolic-H); HRMS (ESI) m/z,
calcd. for C29H18ClN7O2S2 [M + H]+: 596.0730; found: