UYSAL ET AL.
7 of 9
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5-Chloro-3-(((2-methoxyphenyl)amino)methyl)benzo[d]oxazol-
2(3H)-one (3)
5-Chloro-3-(((2-ethylphenyl)amino)methyl)benzo[d]oxazol-
2(3H)-one (8)
Yield 34%; mp 124°C; IR υmax (FT/ATR): 3408, 2993, 2968, 2159,
Yield 10%; mp 122°C; IR υmax (FT/ATR): 3389, 2962, 1772, 1751,
1606, 1588, 1478 cm−1 1H NMR (CDCl3): δ 7.13–7.16 (2H, m, Ar-H),
2032, 1766, 1601, 1482 cm−1
;
1H NMR (DMSO-d6): δ 7.92 (1H, d,
;
J = 2.3 Hz, Ar-H), 7.33 (1H, d, J = 8.3 Hz, Ar-H), 7.15 (1H, dd, J = 8.3;
2.0 Hz, Ar-H), 6.84 (2H, m, Ar-H), 6.76 (1H, t, J = 7.6 Hz, Ar-H), 6.62
(1H, t, J = 7.6 Hz, Ar-H), 6.57 (1H, t, J = 7.2 Hz, NH), 5.26 (2H, d,
J = 7.2 Hz, CH2), 3.79 (3H, s, OCH3) ppm; Anal. calcd. for
7.04–7.09 (3H, m, Ar-H), 6.95 (1H, d, J = 7.2 Hz, Ar-H), 6.79–6.83
(1H, m, Ar-H), 5.36 (2H, d, J = 7.2 Hz, CH2), 4.66 (1H, t, J = 7.2 Hz, NH),
2.52 (2H, q, J = 7.6 Hz, CH2CH3), 1.22 (3H, t, J = 7.6 Hz, CH2CH3) ppm;
Anal. calcd. for C16H15ClN2O2: C, 63.47; H, 4.99; N, 9.25. Found: C,
63.75; H, 5.25; N, 9.40; MS (APCI) m/z (%): 135 (24), 118 (100), 106
(18), 94 (32), 93 (26), 91 (12), 56 (17), 42 (23).
C15H13ClN2O3: C, 59.12; H, 4.30; N, 9.19. Found: C, 59.45; H, 4.36;
N, 9.20; MS (APCI) m/z (%): 161 (13), 150 (6), 120 (44), 109 (100), 81
(10), 80 (48), 65 (8), 42 (7).
5-Chloro-3-(((2-isopropylphenyl)amino)methyl)benzo[d]oxazol-
2(3H)-one (9)
5-Chloro-3-(((2-chlorophenyl)amino)methyl)benzo[d]oxazol-
2(3H)-one (4)
Yield 28%; mp 136°C; IR υmax (FT/ATR): 3454, 3423, 3064, 2955,
1775, 1752, 1603, 1480 cm−1 1H NMR (CDCl3): δ 7.13–7.18 (3H, m,
;
Yield 11%; mp 131°C; IR υmax (FT/ATR): 3379, 2939, 2161, 1772,
;
1595, 1483 cm−1 1H NMR (CDCl3): δ 7.25 (1H, d, J = 8.4 Hz, Ar-H),
Ar-H), 7.05–7.08 (2H, m, Ar-H), 6.97–6.99 (1H, m, Ar-H), 6.85–6.87
(1H, m, Ar-H), 5.39 (2H, d, J = 4.8 Hz, CH2), 4.83 (1H, t, J = 4.4 Hz, NH),
2.89–2.96 (1H, m, CH), 1.25 (6H, d, J = 4.4 Hz, 2xCH3) ppm; Anal. calcd.
for C17H17ClN2O2. 0.1 CH4O: C, 64.19; H, 5.48; N, 8.75. Found: C,
64.18; H, 5.87; N, 8.61; MS (APCI) m/z (%): 317 (1) [M+H]+, 132 (29),
118 (15), 106 (15), 94 (12), 91 (100), 65 (3), 42 (3).
7.16–7.20 (2H, m, Ar-H), 7.07–7.11 (3H, m, Ar-H), 6.75-6-77 (1H, m,
Ar-H), 5.38 (2H, d, J = 4.4 Hz, CH2), 5.28 (1H, t, J = 4.4 Hz, NH) ppm;
Anal. calcd. for C14H10Cl2N2O2: C, 54.39; H, 3.26; N, 9.06. Found: C,
54.55; H, 3.12; N, 9.12; MS (APCI) m/z (%): 142 (4), 140 (12), 135 (24),
118 (40), 110 (52), 94 (16), 81 (15), 56 (100), 42 (24).
5-Chloro-3-(((2-iodophenyl)amino)methyl)benzo[d]oxazol-
2(3H)-one (5)
5-Chloro-3-(((2,6-dimethylphenyl)amino)methyl)benzo[d]oxazol-
2(3H)-one (10)
Yield 8%; mp 121°C; IR υmax (FT/ATR): 3381, 2975, 2160, 2040, 1753,
;
1608, 1480 cm−1 1H NMR (CDCl3): δ 7.65 (1H, d, J = 8.0 Hz, Ar-H),
Yield 20%; mp 133°C; IR υmax (FT/ATR): 3375, 2960, 2867, 1796,
;
1775, 1752, 1609, 1479 cm−1 1H NMR (CDCl3): δ 7.02 (1H, d,
7.24–7.27 (1H, m, Ar-H), 7.17 (1H, d, J = 1.2 Hz, Ar-H), 7.09–7.11
(2H, m, Ar-H), 7.01 (1H, d, J = 8.0 Hz, Ar-H), 6.56 (1H, t, J = 8.0 Hz, Ar-
H), 5.36 (2H, d, J = 6.8 Hz, CH2), 5.12 (1H, bs, NH) ppm; Anal. calcd. for
J = 7.6 Hz, Ar-H), 6.96–6.98 (3H, m, Ar-H), 6.90–6.94 (2H, m, Ar-H),
5.06 (2H, d, J = 7.6 Hz, CH2), 3.99 (1H, bs, NH), 2.22 (6H, s, 2xCH3)
ppm; Anal. calcd. for C16H15ClN2O2: C, 63.47; H, 4.99; N, 9.25.
Found: C, 63.70; H, 5.05; N, 9.37; MS (APCI) m/z (%): 303 (1) [M+H]+,
146 (18), 144 (46), 135 (30), 118 (100), 105 (62), 94 (62), 91 (12), 56
(14), 42 (22).
C14H10ClN2O2I. 1.1 C2H6O: C, 43.12; H, 3.71; N, 6.21. Found: C,
43.52; H, 3.47; N, 5.98; N, 7.56; MS (APCI) m/z (%): 145 (32), 134 (10),
118 (18), 105 (26), 93 (100), 78 (28), 56 (20), 42 (68).
5-Chloro-3-(((2-nitrophenyl)amino)methyl)benzo[d]oxazol-
2(3H)-one (6)
3-((Benzylamino)methyl)-5-chlorobenzo[d]oxazol-2(3H)-one
(11)
Yield 23%; mp 145°C; IR υmax (FT/ATR): 3382, 2978, 1774, 1611,
1480 cm−1; 1H NMR (CDCl3): δ 8.38–8.43 (1H, m, Ar-H), 8.20 (2H, dd,
J = 8.7; 1.6 Hz, Ar-H), 7.51 (1H, td, J = 8.4; 1.6 Hz, Ar-H), 7.99 (1H, d,
J = 8.0 Hz, Ar-H), 6.77–6.81 (2H, m, Ar-H), 6.01–6.10 (1H, bs, NH),
5.13 (1H, t, J = 5.6 Hz, CH2) ppm; Anal. calcd. for C14H10ClN3O4. 0.5
H2O: C, 51.15; H, 3.37; N, 12.78. Found: C, 50.76; H, 3.12; N, 12.84;
MS (APCI) m/z (%): 319 (1) [M]+, 84 (38), 83 (34), 56 (100), 42 (98).
Yield 28%; mp 177°C; IR υmax (FT/ATR): 3067, 3028, 2869, 1798,
;
1776, 1610, 1482 cm−1 1H NMR (CDCl3): δ 7.29–7.33 (5H, m, Ar-H),
7.03–7.04 (2H, m, Ar-H), 6.54–6.61 (1H, m, Ar-H), 4.84 (2H, s,
─CH2NH─), 3.91 (3H, s, CH2-Phenyl and NH) ppm; Anal. calcd. for
C15H13ClN2O2: C, 62.40; H, 4.54; N, 9.70. Found: C, 62.35; H, 4.18; N,
9.30; MS (APCI) m/z (%): 132 (64), 106 (68), 91 (100), 67 (18), 65 (68),
42 (21).
5-Chloro-3-(((2-hydroxyphenyl)amino)methyl)benzo[d]oxazol-
2(3H)-one (7)
3-((1H-Imidazol-1-yl)methyl)-5-chlorobenzo[d]oxazol-2(3H)-one
(12)
Yield 8%; mp 167°C; IR υmax (FT/ATR): 3338, 2975, 2159, 2031, 1747,
1607, 1480 cm−1 1H NMR (CDCl3): δ 7.09–7.11 (3H, m, Ar-H), 6.97
;
Yield 18%; mp 161°C; IR υmax (FT/ATR): 3391, 2082, 1754, 1607,
;
1471 cm−1 1H NMR (CDCl3): δ 7.20–7.21 (1H, m, Ar-H), 7.13–7.14
(1H, d, J = 8.0 Hz, Ar-H), 6.83–6.87 (1H, m, Ar-H), 6.73–6.74 (2H, m,
Ar-H), 5.31 (2H, d, J = 7.2 Hz, CH2), 4.95 (1H, bs, NH) ppm; Anal. calcd.
for C14H11ClN2O3. 0.3 H2O: C, 56.79; H, 3.95; N, 9.46. Found: C,
56.39; H, 3.58; N, 9.85; MS (APCI) m/z (%): 289 (1) [M–H]+, 106 (58), 94
(30), 65 (22), 56 (100), 42 (56).
(2H, m, Ar-H), 7.09–7.12 (3H, m, Ar-H), 5.37 (2H, s, CH2) ppm; Anal.
calcd. for C11H8ClN3O2. 0.25 H2O: C, 51.98; H, 3.37; N, 16.53. Found:
C, 51.60; H, 3.22; N, 16.36; MS (APCI) m/z (%): 251 (1) [M+2H]+, 84
(28), 80 (74), 42 (100).