PAPER
Synthesis of 2,3-Dihydroimidazo[2,1-b][1,3]oxazoles
2695
Table 4 MS, IR and NMR Data of Imidazoles 18a–f and 22
Product
MS
IR (KBr) (cm–1)
1H NMR (CDCl3/TMS)
13C NMR (CDCl3/TMS)
m/z (%)
, J (Hz)
18a
464 ([M + 2]+, 33), 463 ([M 3239, 3067, 2927, 2853, 2.68 (s, 1 H, OH), 4.13,
+ 1]+, 100), 462 ([M]·+, 25), 1603, 1545, 1491, 1451, 4.41 (s, CH2), 6.90 (s, 1 H, 118.3 (d, CHimid), 124.7, 126.2,
40.6, 55.2 (2 t, 2 CH2), 77.64 (s, C),
280 (12), 247 (14), 190 (29), 1337, 1231, 1058, 758
189 (16), 183 (15), 154 (16),
136 (17)
CHimid), 7.17–7.74 (m, 20
H)
126.6, 127.3, 127.7, 128.3, 128.4,
128.5, 128.8 (9 d, 20 CHarom), 133.9,
138.0, 141.5, 141.9, 143.6 (5 s, 6
Carom
)
18b
18c
18d
402 ([M + 2]+, 27), 401 ([M 3371, 3153, 3059, 2983, 1.48 (s, 3 H), 2.23 (s, 1 H,
+ 1]+, 100), 400 ([M]·+, 31), 2929, 1487, 1384, 1197, OH), 3.8 (d, 1 H, J = 14.2), 74.5 (s, C), 118.3 (d, CHimid), 127.7,
26.7 (q, CH3), 40.3, 56.8 (2 t, 2 CH2),
190 (22)
1114, 1070, 952, 754,
701
3.99 (d, 1 H, J = 14.2), 4.20 124.9, 126.7, 127.3, 127.6, 128.5,
(d, 1 H, J = 12.6), 4.27 (d, 1 128.6, 128.8 (8 d, 15 CHarom), 133.9,
H, J = 12.6), 7.05–7.45 (m, 137.7, 141.8, 144.4 (4 s, 5 Carom
)
14 H), 7.80–7.85 (m, 2 H)
533 ([M + 2]+, 69), 532 ([M 3402, 3085, 1600, 1488, 3.48 (s, 1 H), 4.21 (s, 1 H), 38.6, 54.6 (2 t, 2 CH2), 76.2 (s, C),
+ 1]+, 32), 531 ([M]·+, 100), 1448, 1399, 1196, 1092, 4.63 (m, 2 H), 6.48 (s, 1 H), 119.3 (d, CHimid), 125.6, 126.2,
307 (45), 282 (31), 281 (27), 1013, 951, 831, 766
179 (16), 178 (22), 166 (37),
165 (45)
7.42–7.81 (m, 18 H)
127.1, 127.2, 127.7, 128.0, 128.2,
128.3, 128.5, 128.7 (10d, 18 CHarom),
130.6, 131.7, 132.9, 137.8, 138.6,
142.1, 143.5, 144.4 (8 s, 8 Carom
)
471 ([M + 2]+, 69), 470 ([M 3316, 2929, 1663, 1599, 1.46 (s, 3 H), 2.2 (s, 1 H,
+ 1]+, 32), 469 ([M]·+, 100), 1551, 1490, 1448, 1397, OH), 3.75 (d, 1 H, J = 14.2), 74.2 (s, C), 118.4 (d, CHimid), 126.0,
26.7 (q, CH3), 40.2, 56.6 (2 t, 2 CH2),
190 (35), 312 (15)
1193, 1050, 1011, 950,
833, 767, 699
3.95 (d, 1 H, J = 14.4), 4.22 126.5, 127.5, 128.5, 128.7, 128.8 (6
(d, 1 H, J = 13.6), 4.25 (d, 1 d, 13 CHarom), 132.3, 133.6, 137.6,
H, J = 13.6), 7.15–7.40 (m, 140.8, 142.2, 142.8 (6 s, 7 Carom
)
11 H), 7.7–7.75 (m, 2 H)
18e
18f
278 ([M + 2]+, 45), 277 ([M 3249, 2971, 2931,
+ 1]+, 100), 276 ([M]·+, 37), 16565, 1411, 1291,
1.10 (s, 6 H), 2.26 (s, 3 H), 13.7 (q, 2 CH3), 27.0 (q, CH3), 40.5,
3.2 (s, 1 H, OH), 3.57 (s, 2 56.0 (2 t, 2 CH2), 70.7 (s, C), 119.1
H), 4.15 (s, 2 H), 6.83 (s, 1 (d, CHimid), 127.3, 128.4, 128.7 (3 d,
H), 7.10-7.25 (m, 5 H) 5 CHarom), 137.5, 138.4, 139.8 (3s, 3
Carom
217 (25), 94 (17)
1191, 914, 767
)
340 ([M + 2]+, 22), 339 ([M 3157, 3028, 2976, 2931, 1.44 (s, 3 H), 2.1 (s, 1 H,
13.82, 26.76 (q, CH3), 40.44, 56.53
+ 1]+, 100), 338 ([M]·+, 18), 1493, 1450, 1410, 1291, OH), 2.24 (s, 3 H), 3.74 (d, (t, CH2), 74.47 (s, C), 119.13 (d,
341 (7) 1146, 1070, 763 1 H, J = 14.4), 3.94 (d, 1 H, CHimid), 124.89, 125.07, 127.32,
J = 14.4), 4.14 (d, 1 H, J = 128.38, 128.45, 128.8 (d, CHarom),
1.2), 4.17 (d, 1 H, J = 1.6), 137.59, 138.44, 140.17, 144.64 (q,
6.65 (s, 1 H), 7.18–7.4 (m,
14 H)
Carom)
22
388 ([M + 2]+, 6), 387 ([M + 3438, 3063, 1600, 1492, 3.74 (dd, 1 H, J = 14.0, 8.8), 40.85 (t, CH2), 54.5 (t, CH2), 73.0 (d,
1]+, 24), 386 ([M]+, 8), 293
1454, 1412, 1190, 1061, 3.9 (dd, 1 H, J = 14.0, 3.3), CH), 118.6, 124.6, 125.8, 126.6,
(24), 279 (10), 266 (21), 265 751, 696
(100), 264 (23), 247 (16),
145 (18), 121 (12), 105 (13),
93 (46), 92 (25), 91 (31), 79
(15), 63 (11), 55 (17)
4.15 (s, 2 H), 4.8 (s, 1 H,
OH), 4.96 (dd, 1 H, J = 8.8, 128.75 (10 d, 10 CHarom), 133.45,
3.3), 7.1–7.65 (m, 16 H) 137.7, 140.2, 141.05,141.6 (5 s, 5
Carom
127.3, 127.9, 128.4, 128.45, 128.5,
)
Table 5 Imidazole Sulfone Derivatives 19a–d and 23 Prepared
Entry
Producta
19a
R
R1
Yield (%)
mp (°C)
172–173
127–128
198–199
165–166
134–135
1
2
3
4
5
Ph
Ph
Me
Ph
Me
-
60
52
58
50
68
19b
Ph
19c
p-ClC6H4
p-ClC6H4
-
19d
23
a Satisfactory microanalyses obtained: C 0.21, H 0.19, N 0.27, S 0.29.
Synthesis 2002, No. 18, 2691–2700 ISSN 0039-7881 © Thieme Stuttgart · New York