Sep-Oct 2002
Heterocyclization Reaction of 2-(2-Methylaziridin-1-yl)-3-ureidopyridines
979
Table 3
1
H NMR Data of Compounds 12, 16 and 17
12a
12b
1.19 (d, 3H, J = 5.2 Hz), 2.02 (m, 1H), 2.52 (m, 2H), 6.97-7.01 (m, 1H), 7.12-7.18 (m, 1H), 7.32-7.39 (m, 4H), 7.68 (s, 1H), 7.91-7.93 (m,
1H), 8.02 (s, 1H), 8.39-8.42 (m, 1H)
1.26 (d, 3H, J = 4.9 Hz), 2.11 (m, 1H), 2.56 (m, 2H), 6.98-7.03 (m, 1H), 7.28-7.30 (m, 4H), 7.77 (s, 1H), 7.94-7.96 (m, 1H), 8.11 (s, 1H), 8.31-
8.34 (m, 1H)
12c
12d
1.29 (d, 3H, J = 5.2 Hz), 2.11 (m, 1H), 2.57 (m, 2H), 6.98-7.17 (m, 4H), 7.39 (s, 1H), 7.93-7.99 (m, 2H), 8.01 (s, 1H), 8.35-8.38 (m, 1H)
1.17 (d, 3H, J = 5.2 Hz), 2.02 (m, 1H), 2.50 (m, 2H), 3.83 (s, 3H), 6.91(d, 2H, J = 8.9 Hz), 6.98-7.02 (m, 1H), 7.29 (d, 2H, J = 8.9 Hz), 7.52 (s,
1H), 7.91-7.93 (m, 1H), 8.04 (s, 1H), 8.45-8.48 (m, 1H)
12e
12f
1.42 (d, 3H, J = 5.5 Hz), 2.41 (d, 1H, J = 4.0 Hz), 2.50 (d, 1H, J = 6.4 Hz), 2.77 (m, 1H), 6.98-7.02 (m, 1H), 7.51-7.65 (m, 3H), 7.99-8.03 (m,
3H), 8.51-8.53 (m, 1H), 9.16 (s, 1H), 11.46 (s, 1H)
1.41 (d, 3H, J = 5.5 Hz), 2.40 (d, 1H, J = 4.0 Hz), 2.51 (d, 1H, J = 6.4 Hz), 6.99-7.03 (m, 1H), 7.47-7.51 (m, 2H), 8.01-8.05 (m, 3H), 8.44-8.47
(m, 1H), 9.97 (s, 1H), 11.50 (s, 1H)
12g
16a
16b
16c
16d
16e
16f
1.42 (d, 3H, J = 5.5 Hz), 2.41 (d, 1H, J = 4.0 Hz), 2.45 (s, 3H), 2.49 (d, 1H, J = 6.1 Hz), 2.77 (m, 1H), 6.97-7.01 (m, 1H), 7.32 (d, 2H, J = 8.0
Hz), 7.87 (d, 2H, J = 8.0 Hz), 8.00-8.02 (m, 1H), 8.51-8.54 (m, 1H), 8.87 (s, 1H), 11.43 (s, 1H)
1.64 (d, 3H, J = 6.7 Hz), 4.27 (dd, 1H, J = 15.3 and 8.1 Hz), 4.51 (dd, 1H, J = 15.3 and 3.4 Hz), 4.60 (m, 1H), 7.01-7.12 (m, 2H), 7.29-7.35 (m,
2H), 7.56-7.58 (m, 2H), 7.74-7.76 (m, 1H), 8.08-8.10 (m, 1H)
1.62 (d, 3H, J = 6.7 Hz), 4.25 (dd, 1H, J = 15.3 and 8.2 Hz), 4.50 (dd, 1H, J = 15.3 and 3.4 Hz), 4.59 (m, 1H), 7.09-7.13 (m, 1H), 7.24 (d, 2H, J
= 8.9 Hz), 7.50 (d, 2H, J = 8.9 Hz), 7.73-7.75 (m, 1H), 8.10-8.12 (m, 1H)
1.70 (d, 3H, J = 6.7 Hz), 4.29 (dd, 1H, J = 15.3 and 8.4 Hz), 4.58 (dd, 1H, J = 15.3 and 3.0 Hz), 4.67 (m, 1H), 6.98-7.21 (m, 3H), 7.39 (s, 1H),
7.78-7.81 (m, 1H), 8.12-8.14 (m, 1H), 8.37-8.43 (m, 1H)
1.70 (d, 3H, J = 6.7 Hz), 3.81 (s, 3H), 4.27 (dd, 1H, J = 15.3 and 8.2 Hz), 4.56 (dd, 1H, J = 15.3 and 3.1 Hz), 4.66 (m, 1H), 6.93 (d, 2H, J = 8.9
Hz), 7.07-7.12 (m, 1H), 7.48 (d, 2H, J = 8.9 Hz), 7.72-7.75 (m, 1H), 8.06-8.08 (m, 1H)
1.65 (d, 3H, J = 6.7 Hz), 4.48 (dd, 1H, J = 13.7 and 6.3 Hz), 4.67 (dd, 1H, J = 13.7 and 7.9 Hz), 4.85 (m, 1H), 7.14-7.18 (m, 1H), 7.43-7.55 (m,
4H), 8.26-8.35 (m, 3H)
1.65 (d, 3H, J = 6.7 Hz), 4.46 (dd, 1H, J = 13.7 and 6.3 Hz), 4.66 (dd, 1H, J = 13.7 and 7.9 Hz), 4.82 (m, 1H), 7.17-7.21 (m, 1H), 7.41-7.55 (m,
3H), 8.24-8.29 (m, 3H)
16g
17a
17b
17c
17d
1.64 (d, 3H, J = 6.4 Hz), 2.43 (s, 3H), 4.47 (dd, 1H, J = 13.7 and 6.4 Hz), 4.66 (dd, 1H, J = 13.7 and 7.6 Hz), 4.84 (m, 1H), 7.15-7.28 (m, 3H),
7.52-7.54 (m, 1H), 8.20-8.27 (m, 3H)
1.58 (d, 3H, J = 6.1 Hz), 4.05 (dd, 1H, J = 9.8 and 4.0 Hz), 4.49 (dd, 1H, J = 9.8 and 8.5 Hz), 5.11 (m, 1H), 7.04-7.12 (m, 2H), 7.40-7.74 (m,
4H), 8.04-8.06 (m, 1H)
1.53 (d, 3H, J = 6.4 Hz), 4.02 (dd, 1H, J = 10.0 and 3.7 Hz), 4.44 (dd, 1H, J = 10.0 and 8.8 Hz), 5.03 (m, 1H), 7.04-7.08 (m, 1H), 7.30-7.73 (m,
4H), 8.04-8.06 (m, 1H)
1.43 (d, 3H, J = 6.4 Hz), 4.01 (dd, 1H, J = 10.1 and 5.6 Hz), 4.55 (dd, 1H, J = 10.1 and 8.5 Hz), 5.14 (m, 1H), 7.01-7.06 (m, 1H), 7.19-7.89 (m,
4H), 8.02-8.05 (m, 1H)
1.53 (d, 3H, J = 6.1 Hz), 3.82 (s, 3H), 4.01 (dd, 1H, J = 9.8 and 4.9 Hz), 4.50 (dd, 1H, J = 9.8 and 8.5 Hz), 5.01 (m, 1H), 6.95-7.05 (m, 3H),
7.54-7.59 (m, 1H), 7.65-7.68 (m, 1H), 8.00-8.03 (m, 1H)
Table 4
13
C NMR and Mass Spectra Data of Compounds 16 and 17
13
C nmr d(ppm)
Mass spectra
m/z (%)
(Deuteriochloroform)
+
16a
16b
16c
16d
16e
16f
22.6, 49.5, 57.4, 118.2, 119.2, 123.1, 123.7, 129.2, 134.7,
139.0, 140.4, 147.4, 151.0
22.5, 49.4, 57.3, 118.3, 120.4, 123.7, 127.9, 129.0, 134.4,
137.6, 140.6, 147.1, 150.6
22.6, 49.8, 57.4, 114.8 (d), 118.3, 120.1, 122.7, 124.1,
124.7 (d), 134.6, 140.8, 147.3, 150.2, 150.8, 154.1
22.5, 49.2, 55.4, 56.8, 114.0, 114.8, 121.6, 122.5,
131.9, 134.8, 140.6, 147.5, 152.1, 156.0
22.6, 47.8, 54.8, 118.8, 119.1, 122.7, 128.1, 128.9,
131.5, 137.7, 142.6, 142.9, 152.7, 174.2
250 (M , 100), 249 (33), 235 (65), 209 (43), 135 (13), 117 (11)
+
+
286 (M , 39), 285 (34), 284 (M , 100), 283 (29), 271 (23),
269 (64), 245 (9), 243 (27), 208 (38), 153 (11), 151 (15), 135 (37)
+
268 (M , 100), 267 (21), 253 (44), 228 (54),
227 (29), 209 (47), 159 (12), 135 (12)
+
280 (M , 100), 279 (13), 265 (62), 250 (16),
239 (12), 147 (55), 135 (15)
+
278 (M , 33), 277 (60), 173 (35), 105 (100), 77 (46)
+
+
22.5, 47.7, 54.4, 118.7, 122.6, 128.0, 130.6, 136.3,
138.0, 142.8, 151.2, 152.5, 167.6, 173.0
314 (M , 7), 313 (13), 312 (M , 23), 311 (30),
209 (7), 207 (16), 173 (32), 141 (34), 139 (100), 113 (10), 111 (29)
+
16g
17a
17b
17c
17d
21.6, 22.6, 48.2, 53.6, 117.7, 118.6, 122.0, 128.8,
129.4, 134.7, 142.3, 143.1, 143.3, 154.1, 177.4
19.4, 46.8, 59.1, 117.4, 117.8, 122.7, 123.7, 128.5,
129.4, 131.9, 138.0, 140.1, 140.8, 145.8, 157.0
19.1, 46.6, 59.0, 117.4, 118.5, 123.7, 127.3, 128.3,
129.2, 131.8, 136.5, 140.2, 140.5, 145.5, 156.3
19.3, 47.1, 61.6, 116.8 (d), 117.3, 123.6, 125.0, 126.7,
127.2 (d), 128.4 (d), 132.0, 133.2, 139.9, 146.1, 154.7
19.1, 46.6, 55.4, 59.8, 114.6, 117.1, 120.5, 123.1,
128.3, 130.9, 131.9, 139.6, 140.8, 145.9, 155.7, 157.6
292 (M , 35), 291 (59), 173 (28), 119 (100), 91 (43)
+
250 (M , 100), 249 (29), 235 (44), 209 (29), 135 (11)
+
+
286 (M , 33), 285 (27), 284 (M , 100), 283 (28),
271 (20), 269 (58), 243 (27), 208 (40), 135 (33)
+
268 (M , 100), 267 (14), 253 (40), 227 (15), 159 (12), 135 (10)
+
280 (M , 100), 279 (13), 265 (63), 250 (15), 147(52), 135 (15)