Med Chem Res
1
2911, 2847, 1602, 1551, 1218, 1052. H NMR (CDCl3):
δ = 1.84 (m, 6H, Hadamantane), 2.19 (m, 9H, Hadamantane),
7.37 (m, 1H, Harom.), 7.62 (m, 1H, Harom.), 7.97 (m, 1H,
42.2 (3 × Cadamantane), 121.3 (C5thiazole), 124.2, 127.5, 129.0,
131.7, 132.5, 139.0 (6 × Carom.), 141.1 (C4thiazole), 160.7
(C5oxadiazole), 165.0 (C2thiazole), 170.2 (C2oxadiazole). EI-MS
(m/z, %): 391 ([M]+, 28), 202 (19), 174 (4), 135 (100), 117
(3), 107 (7), 93 (18), 91 (11), 79 (10). Anal. Calcd. for
C23H25N3OS: C, 70.56; H, 6.44; N, 10.73. Found: C, 70.38;
H, 6.37; N, 10.48.
H
arom.), 8.14 (s, 1H, Hthiazole), 8.26 (m, 1H, Harom.). 13C
NMR (CDCl3): δ = 27.7, 34.5, 36.3, 39.9 (10 × Cadamantane),
121.9 (C5thiazole), 123.2, 125.6, 129.7, 130.6, 133.7, 134.4
(6 × Carom.), 141.6 (C4thiazole), 160.1 (C5oxadiazole), 167.9
(C2thiazole), 172.8 (C2oxadiazole). EI-MS (m/z, %): 443 ([M
+2]+, 98), 441/443 ([M]+, 100), 268 (10), 266 (12), 240 (4),
238 (3), 135 (79), 107 (6), 93 (14), 79 (14). Anal. Calcd. for
C21H20BrN3OS: C, 57.02; H, 4.56; N, 9.50. Found: C,
56.90; H, 4.50; N, 9.39.
2-[((Adamantan-1-yl)methyl)-5-(2-(4-methylphenyl)-1,3-
thiazol-4-yl)]-1,3,4-oxadiazole (7o) From 5c (117 mg).
Yield: 141 mg (72 %); Mp 188–190 °C; FTIR (νmax, cm−1):
1
3108, 2901, 2847, 1585, 1562, 1222. H NMR (CDCl3): δ
= 1.61–1.74 (m, 12H, Hadamantane), 2.01 (br s, 3H,
2-[(Adamantan-1-yl)-5-(2-(4-bromophenyl)-1,3-thiazol-4-
yl)]-1,3,4-oxadiazole (7l) From 5l (149 mg). Yield: 179
mg (81 %); Mp 206–207 °C; FTIR (νmax, cm−1): 3091,
Hadamantane), 2.43 (s, 3H, Ar–Me), 2.76 (s, 2H, CH2), 7.29
(d, 2H, J = 8.1 Hz, Harom.), 7.95 (d, 2H, J = 8.1 Hz, Harom.),
8.07 (s, 1H, Hthiazole). 13C NMR (CDCl3): δ = 21.5 (CH3),
28.5, 33.6, 36.6 (7 × Cadamantane), 39.6 (CH2), 42.2 (3 ×
1
2922, 2848, 1603, 1552, 1208, 1049. H NMR (CDCl3): δ
= 1.84 (m, 6H, Hadamantane), 2.18 (m, 9H, Hadamantane),
7.61–7.64 (m, 2H, Harom.), 7.93–7.96 (m, 2H, Harom.), 8.12
(s, 1H, Hthiazole). 13C NMR (CDCl3): δ = 27.7, 34.5, 36.3,
39.9 (10 × Cadamantane), 121.6 (C5thiazole), 125.3, 128.4,
C
adamantane), 121.0 (C5thiazole), 126.9, 129.7, 130.0, 141.0
(6 × Carom.), 141.3 (C4thiazole), 160.8 (C5oxadiazole), 165.0
(C2thiazole), 170.2 (C2oxadiazole). EI-MS (m/z, %): 391 ([M]+,
16), 202 (11), 174 (3), 135 (100), 117 (3), 107 (8), 93 (25),
91 (14), 79 (32). Anal. Calcd. for C23H25N3OS: C, 70.56;
H, 6.44; N, 10.73. Found: C, 70.29; H, 6.36; N, 10.56.
131.6, 132.3 (6 × Carom.), 141.6 (C4thiazole), 160.1 (C5
oxadia-
2
zole), 168.5 (C thiazole), 172.7 (C2oxadiazole). EI-MS (m/z, %):
443/445 ([M+2]+, 98), 440/442 ([M]+, 100), 268 (10), 266
(11), 240 (3), 238 (3), 135 (45), 107 (4), 93 (7), 79 (6).
Anal. Calcd. for C21H20BrN3OS: C, 57.02; H, 4.56; N,
9.50. Found: C, 56.85; H, 4.47; N, 9.29.
2-[((Adamantan-1-yl)methyl)-5-(2-(2-fluorophenyl)-1,3-
thiazol-4-yl)]-1,3,4-oxadiazole (7p) From 5d (119 mg).
Yield: 140 mg (71 %); Mp 173–175 °C; FTIR (νmax, cm−1):
3096, 2905, 2845, 1604, 1563, 1207, 1192. 1H NMR
(CDCl3): δ = 1.60–1.72 (m, 12H, Hadamantane), 2.00 (br s,
3H, Hadamantane), 2.74 (s, 2H, CH2), 7.18–7.32 (m, 2H,
2-[((Adamantan-1-yl)methyl)-5-(2-(2-methylphenyl)-1,3-
thiazol-4-yl)]-1,3,4-oxadiazole (7m) From 5a (117 mg).
Yield: 143 mg (73 %); Mp 152–154 °C; FTIR (νmax, cm−1):
H
arom.), 7.44 (m, 1H, Harom.), 8.21 (s, 1H, Hthiazole), 8.46 (m,
1
3106, 2921, 2847, 1599, 1562, 1206. H NMR (CDCl3): δ
1H, Harom.). 13C NMR (CDCl3): δ = 28.5, 33.6, 36.5 (7 ×
= 1.61–1.74 (m, 12H, Hadamantane), 2.01 (br s, 3H,
Cadamantane), 39.6 (CH2), 42.2 (3 × Cadamantane), 116.1 (d,
H
adamantane), 2.65 (s, 3H, Ar–Me), 2.75 (s, 2H, CH2),
JC-F = 21.75 Hz, C3arom.), 120.4 (d, JC-F = 11.25 Hz,
C1arom.), 121.2 (C5thiazole), 122.7 (d, JC-F = 9.75 Hz,
7.29–7.42 (m, 3H, Harom.), 7.78 (m, 1H, Harom.), 8.19
(s, 1H, Hthiazole). 13C NMR (CDCl3): δ = 21.5 (CH3),
28.5, 33.6, 36.5 (7 × Cadamantane), 39.5 (CH2), 42.2
(3 × Cadamantane), 122.1 (C5thiazole), 126.2, 130.1, 131.5,
131.6, 132.0, 136.9 (6 × Carom.), 140.5 (C4thiazole), 160.8
(C5oxadiazole), 165.1 (C2thiazole), 169.5 (C2oxadiazole). EI-MS
(m/z, %): 391 ([M]+, 16), 202 (9), 174 (13), 135 (100), 117
(4), 107 (12), 93 (29), 91 (16), 79 (29). Anal. Calcd. for
C23H25N3OS: C, 70.56; H, 6.44; N, 10.73. Found: C, 70.33;
H, 6.36; N, 10.54.
C6arom.), 124.8 (d, JC-F = 3.0 Hz, C5arom.), 132.0 (d, JC-F
=
9.0 Hz, C4arom.), 140.2 (C4thiazole), 160.2 (d, JC-F = 250.5
Hz, C2arom.), 160.8 (C5oxadiazole), 162.2 (C2thiazole), 165.1
(C2oxadiazole). EI-MS (m/z, %): 394/396 ([M]+, 12), 206 (18),
178 (3), 135 (100), 121 (3), 107 (12), 93 (31), 79 (64). Anal.
Calcd. for C22H22FN3OS: C, 66.81; H, 5.61; N, 10.62.
Found: C, 66.63; H, 5.58; N, 10.50.
2-[((Adamantan-1-yl)methyl)-5-(2-(3-fluorophenyl)-1,3-
thiazol-4-yl)]-1,3,4-oxadiazole (7q) From 5e (119 mg).
Yield: 146 mg (74 %); Mp 156–158 °C; FTIR (νmax, cm−1):
3106, 2903, 2845, 1603, 1564, 1210, 1197. 1H NMR
(CDCl3): δ = 1.61–1.73 (m, 12H, Hadamantane), 2.01 (br s,
3H, Hadamantane), 2.76 (s, 2H, CH2), 7.18 (m, 1H, Harom.),
7.46 (m, 1H, Harom.), 7.80 (m, 1H, Harom.), 8.14 (s, 1H,
2-[((Adamantan-1-yl)methyl)-5-(2-(3-methylphenyl)-1,3-
thiazol-4-yl)]-1,3,4-oxadiazole (7n) From 5b (117 mg).
Yield: 155 mg (79 %); Mp 163–165 °C; FTIR (νmax, cm−1):
1
3083, 2896, 2844, 1581, 1561, 1229. H NMR (CDCl3): δ
= 1.61–1.74 (m, 12H, Hadamantane), 2.01 (br s, 3H,
H
adamantane), 2.45 (s, 3H, Ar–Me), 2.75 (s, 2H, CH2),
H
thiazole). 13C NMR (CDCl3): δ = 28.5, 33.6, 36.5 (7 ×
7.31–7.39 (m, 2H, Harom.), 7.83 (m, 1H, Harom.), 7.91 (m,
1H, Harom.), 8.01 (s, 1H, Hthiazole). 13C NMR (CDCl3): δ =
21.3 (CH3), 28.5, 33.6, 36.5 (7 × Cadamantane), 39.6 (CH2),
Cadamantane), 39.6 (CH2), 42.2 (3 × Cadamantane), 113.8 (d,
JC-F = 23.3 Hz, C4arom.), 117.8 (d, JC-F = 21.8 Hz, C2arom.),
121.9 (C5thiazole), 130.8 (d, JC-F = 3.0 Hz, C6arom.), 134.5