W. Szczepankiewicz et al. / Tetrahedron 56 (2000) 9343±9349
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C, 74.61; H, 6.40 N, 18.71. C14H15N3 requires C, 74.64; H,
6.71; N, 18.65%]; dH 3.36 (3H, s, Me), 5.97 (2H, s, NH2-
aliph.), 6,49±6.54 (1H, m, 5), 6.69±7.72 (1H, m, 3), 6.76±
6.79 (2H, m, 20160), 6.87 (2H, s, NH2-arom.), 7.06±7.15
(3H, m, 4130150), 7.50±7.53 (1H, m, 6); m/z 225 (48, M1),
208 (17), 119 (38), 107 (100), 106 (71), 92 (18), 91 (16), 77
(10), 65 (30), 39 (11%).
[Found: C, 63.49; H, 4.93; N, 17.13. C13H12ClN3 requires C,
63.55; H, 4.92; N, 17.10%]; dH 6.28 (2H, s, NH2-aliph.),
6.53±6.57 (1H, m, 5), 6.73±6.76 (3H, m, NH2-arom.13),
6.85±6.87 (1H, m, 60), 6.93 (1H, s, 20), 4.04±7.06 (1H, m,
40), 7.04±7.06 (1H, m, 40), 7.10±7.15 (1H, m, 4), 7.32±7.37
(1H, m, 50), 7.54±7.56 (1H, m, 6); m/z 245 (19, M1), 228
(23), 129 (28), 127 (85), 119 (100), 118 (31), 111 (12), 105
(19), 92 (49), 91 (24), 75 (27), 66 (11), 65 (52), 64 (24), 63
(19), 52 (14), 51 (13), 39 (27%).
1c. (1.22 g, 36%), as a white solid, mp 123±1248C; [Found:
C, 74.93; H, 6.73; N, 18.45. C14H15N3 requires C, 74.64; H,
6.71; N, 18.65%]; dH 2.29 (3H, s, Me), 5.98 (2H, bs, NH2-
aliph.), 6.49±6.54 (1H, m, 5), 6.65±6.71 (3H, m, 3120140),
6.80±6.83 (3H, m, NH2-arom.150), 7.07±7.11 (1H, m, 4),
7.18±7.23 (1H, m, 60), 7.49±7.51 (1H, m, 6); m/z 225 (43,
M1), 224 (26), 208 (17), 119 (37), 118 (21), 107 (100), 106
(54), 92 (22), 91 (25), 79 (10), 78 (10), 77 (15), 65 (42), 64
(12), 63 (11), 53 (12), 52(13), 43(10), 41 (29%).
1i. (1.40 g, 38%), as white plates, mp 161±1628C; [Found:
C, 63.60; H 4.81; N 17.05. C13H12ClN3 requires C, 63.55; H,
4.92; N, 17.10%]; dH (acetone-d6) 5.83 (2H, bs, NH2-aliph.),
6.54±6.60 (1H, m, 4), 6.67 (2H, bs, NH2-arom.), 6.77±6.79
(1H, m, 3), 6.92±6.95 (2H, m, 30150), 7.10±7.15 (1H, m, 5),
7.30±7.33 (2H, m, 20160), 7.57±7.59 (1H, m, 6); m/z 245
(42, M1), 228 (19), 129 (31), 127 (100), 119 (82), 118 (32),
105 (17), 92 (45), 91 (26), 75 (22), 65 (48), 64 (18), 63 (17),
53 (11), 52 (12), 41 (26), 40 (12%).
1d. (2.06 g, 61%), as a white solid, mp 152±1538C; [Found:
C, 74.89; H, 6.54; N, 18.61. C14H15N3 requires C, 74.64; H,
6.71; N, 18.65%]; dH 2.27 (3H, s, Me), 5.97 (2H, bs, NH2-
aliph.), 6.49±6.54 (1H, m, 5), 6.69±6.71 (1H, m, 3), 6.76±
6.86 (2H, m, 20160), 6.87 (2H, bs, NH2-arom.), 7.06±7.15
(3H, m, 4 130150), 7.50±7.53 (1H, m, 6); m/z 225 (49, M1),
224 (14), 208 (17), 119 (38), 107 (100), 106 (71), 92 (18), 91
(16), 65 (30), 39 (11%).
1j. (0.21 g, 5%), as a white solid, mp 130±1318C; [Found:
C, 55.80; H, 3.96; N, 14.98. C13H11Cl2N3 requires C, 56.14;
H, 3.99; N, 15.11%]; dH 6.42 (2H, s, NH2-aliph.), 6.49±6.53
(1H, m, 5), 6.69±6.71 (3H, m, NH2-arom.120), 6.84±6.86
(2H, m, 3), 7.10±7.20 (2H, m, 415), 7.49±7.51 (2H, m,
6160); m/z 279 (30, M1), 278 (8), 264 (9), 262 (13), 165
(7), 164 (5), 163 (38), 162 (7), 161 (61), 122 (10), 119 (100),
118 (45), 109 (10), 92 (44), 91 (30), 90 (18), 75 (11), 66
(10), 65 (42), 64 (20), 63 (24), 53 (17), 52 (11), 51 (10), 43
(12), 41 (29), 40 (14%).
1e. (0.68 g, 19%), as white crystals, mp 92±938C; [Found:
C, 75.10; H, 7.13; N 17.56. C15H17N3 requires C, 75.28; H,
7.16; N, 17.56%]; dH (acetone-d6) 2.12 (3H, s, 20-Me), 2.26
(3H, s, 40-Me), 5,50 (2H, s, NH2-aliph.), 6.52±6.57 (1H, m,
5), 6.70±6.72 (1H, m, 3), 6.76±6.79 (3H, m, NH2-
arom.160), 6.96±6.97 (1H, m, 50), 7.02 (1H, s, 30), 7.09±
7.14 (1H, m, 4), 7.55±7.57 (1H, m, 6); m/z 239 (66, M1),
238 (18), 224 (31), 223 (11), 222 (31), 221 (14), 122 (12),
121 (100), 120 (59), 119 (58), 118 (21), 112 (10), 111 (10),
106 (66), 103 (14), 92 (32), 91 (22), 79 (13), 78 (11), 77
(35), 65 (35), 53 (11), 52 (14), 41 (25%).
1k. (2.39 g, 55%), as a white solid, mp 127±1298C; [Found:
C, 53.77; H, 4.25; N, 14.42. C13H12BrN3 requires C, 53.81;
H, 4.17; N, 14.48%]; dH 6.24 (1H, bs, NH2-aliph.), 6.49±
6.45 (1H, m, 5), 6.67±6.72 (1H, m, 3), 6.78 (2H, bs, NH2-
arom.), 6.90±6.98 (2H, m, 50160), 7.08±7.13 (1H, m, 4),
7.23±7.33 (1H, m, 40), 7.49±7.51 (1H, m, 50), 7.60±7.63
(1H, m, 4); m/z 291 (22, (M12)1), 289 (22, M1), 274 (8),
272 (8), 210 (54), 193 (16), 173 (58), 171 (59), 119
(100), 118 (42), 105 (30), 97 (10), 93 (20), 92 (77), 91
(48), 90 (18), 77 (16), 76 (27), 75 (25), 66 (21), 65 (91),
64 (34), 63 (34), 52 (25), 51 (22), 50 (21), 41 (16), 39 (61),
38 (21%).
1f. (1.58 g, 44%), as white needles, mp 109±1128C; [Found:
C, 75.34; H, 7.19; N, 17.62. C15H17N3 requires C, 75.28; H,
7.16; N, 17.56%]; dH 2.18 (3H, s, 30-Me), 2.20 (3H, s, 40-
Me), 5.94 (2H, s, NH2-aliph.), 6.48±6.53 (1H, m, 5), 6.57±
6.60 (1H, m, 3), 6.67±6.71 (2H, m, 5120), 6.87 (2H, s,
NH2-arom.), 6.87±7.11 (2H, m, 4160), 7.48±7.51 (1H, m,
6); m/z 239 (52, M1), 238 (20), 222 (16), 122 (11), 121
(100), 120 (52), 119 (44), 118 (15), 112 (11), 106 (70),
103 (11), 92 (23), 91 (17), 79 (11), 78 (74), 77 (35), 65
(28), 51 (11), 39 (19%).
1l. (1.57 g, 36%), as a white solid, mp 98±998C; [Found: C,
54.01; H, 4.17; N, 14.44. C13H12BrN3 requires C, 53.81; H,
4.17; N, 14.48%]; dH 6.29 (2H, bs, NH2-aliph.), 6.53±6.56
(1H, m, 5), 6.73±6.76 (3H, m, NH2-arom.13), 6.89±6.91
(1H, m, 60), 7.07±7.20 (3H, m, 4120140), 7.26±7.31 (1H,
m, 50), 7.53±7.56 (1H, m, 6); m/z 289 (24, M1), 288 (13),
274 (11), 173 (36), 171 (37), 119 (100), 118 (33), 105 (20),
93 (18), 92 (64), 91 (30), 90 (11), 76 (23), 75 (18), 66 (15),
65 (69), 64 (23), 63 (24), 52 (17), 51 (12), 50 (16), 41 (11),
39 (37), 38 (13%).
1g. (0,77 g, 21%), as a white±yellow solid, mp 123±1258C;
[Found: C, 63.46; H, 4.89; N, 17.17. C13H12ClN3 requires C,
63.55; H, 4.92; N, 17.10%]; dH 6.25 (2H, bs, NH2-aliph.),
6.50±6.55 (1H, m, 5), 6.69±6.72 (1H, m, 3), 6.76 (2H, bs,
NH2-arom.), 6.97±7.02 (2H, m, 50160), 7.08±7.13 (1H, m,
4), 7.24±7.29 (1H, m, 40), 7.43±7.46 (1H, m, 30), 7.49±7.51
(1H, m, 6); m/z 245 (36, M1), 228 (14), 210 (36), 129 (34),
128 (10), 127 (100), 119 (74), 118 (32), 105 (19), 92 (50), 91
(32), 90 (16), 78 (11), 77 (10), 76 (11), 75 (32), 66 (13), 65
(60), 64 (24), 63 (27), 52 (20), 51 (18), 50 (15), 41 (13), 39
(38), 38 (15%).
1m. (1.65 g, 38%), as white plates, mp 167±1688C; [Found:
C, 53.80; H, 4.19; N, 14.40. C13H12BrN3 requires C, 53.81;
H, 4.17; N, 14.48%]; dH 6.20 (2H, bs, NH2-aliph.), 6.49±
6.54 (1H, m, 5), 6.69±6.72 (1H, m, 5), 6.77 (2H, bs, NH2-
arom.), 6.82±6.85 (2H, m, 30150), 7.07±7.12 (1H, m, 4),
7.44±7.47 (2H, m, 20160), 7.50±7.53 (1H, m, 5); m/z 289
(71, M1), 173 (47), 171 (49), 119 (100), 118 (24), 105 (21),
92 (58), 91 (28), 90 (11), 76 (22), 75 (18), 66 (12), 65 (62),
1h. (1.47 g, 40%), as a canary-yellow solid, mp 104±1068C;