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7,9-Diaryl-1,2,4,8-tetraazaspiro[4.5]decan-3-thiones
1447
3J ¼ 11.87 Hz; 2.89 Hz, 2H) H7 and H9, 2.05–2.29 (m, 4H) H6 and H10,
7.32, 7.38 (2d, 8H) aromatic, 8.46 (br. s, 2H) NH-CS-NH, 7.07 (s, 1H)
NH at1, 1.87 (s, 1H) NH at8. 13C NMR (ꢀ ppm): 58.695 (C7, C9), 38.750
(C6, C10), 78.641 (C5), 180.102 (C¼S), 128.252, 128.405, 133.204, 146.742
(aryl carbons). Mass (m/z): 392 (Mþ), (M.F: C18H18N4SCl2), 362, 332,
317, 276, 262, 247, 179, 167, 139 (100%), 111, 95, 75, 65, 50.
6-Methyl-7,9-bis( p-chlorophenyl)-1,2,4,8-tetraazaspiro[4.5]decan-3-
thione (6b). IR (KBr) (cmꢂ1): 3418.8, 3375.3, 3299.4, 2394.6, 1587.7,
1488.4, 1474.1, 1361.7, 1348.4, 1241.0, 1091.3 etc. 1H NMR (ꢀ ppm):
3
3
4.27 (dd, J ¼ 12.00 Hz; 2.67 Hz, 1H) H9, 3.81 (d, J ¼ 10.85 Hz, 1H)
H7, 2.09–2.37 (m, 3H) H6 and H10, 7.34–7.47 (m, 8H) aromatic, 8.44
(br. s, 2H) NH-CS-NH, 6.85(s, 1H) NH at1, 1.90 (s, 1H) NH at8,
0.82 (d, J ¼ 6.57 Hz, 3H) CH3 at6. 13C NMR (ꢀ ppm): 64.847 (C7),
59.362 (C9), 39.833 (C6), 38.002 (C10), 79.301 (C5), 180.907 (C¼S),
12.040 (CH3 at6), 127.288, 128.726, 128.990, 131.364, 131.989,
133.922, 138.920, 146.443 (aryl carbons). Mass (m/z): 406 (Mþ), (M.F:
C19H20N4SCl2), 376, 346, 331, 290, 276, 262, 247, 223, 181, 166, 155, 138
(100%), 111, 94, 75, 65, 55, 50.
7,9-bis(p-Chlorophenyl)-1,2,4,8-tetraazaspiro[4.5]decan-3-thione (7b):
IR (KBr) (cmꢂ1): 3369.3, 3305.2, 2347.3, 1603.9, 1500.7, 1468.1, 1341.0,
1300.8, 1210.4, 1028.9, 1001.0 etc. 1H NMR (ꢀ ppm): 4.24 (dd,
3J ¼ 11.84 Hz; 2.86 Hz, 2H) H7 and H9, 2.02–2.26 (m, 4H) H6 and H10,
6.89, 7.35 (2d, 8H) aromatic, 8.43 (br. s, 2H) NH-CS-NH, 7.17 (s, 1H)
NH at1, 1.91 (s, 1H) NH at8, 3.90 (s, 6H) OCH
.
3
13C NMR (ꢀ ppm):
58.847 (C7, C9), 38.974 (C6, C10), 78.630 (C5), 180.159 (C¼S), 54.618
(OCH3), 115.544, 127.837, 141.903, 158.541 (aryl carbons). Mass (m/z):
384 (Mþ), (M.F: C20H24N4SO2), 354, 324, 309, 268, 254, 239, 175, 163,
134 (100%), 117, 107, 75, 65, 50.
6-Methyl-7,9-bis( p-methoxyphenyl)-1,2,4,8-tetraazaspiro[4.5]decan-3-
thione (8b). IR (KBr) (cmꢂ1): 3429.5, 3351.0, 3313.7, 3294.0, 2349.2,
1584.2, 1501.4, 1474.2, 1420.9, 1384.7, 1320.4, 1270.2, 1201.5, 1134.3,
1
3
1027.4 etc. H NMR (ꢀ ppm): 4.26 (dd, J ¼ 12.02 Hz; 2.63 Hz, 1H) H9,
3.80 (d, 3J ¼ 10.89 Hz, 1H) H7, 2.08–2.35 (m, 3H) H6 and H10, 6.85–6.87,
7.36–7.38 (m, 8H) aromatic, 8.44 (br. s, 2H) NH-CS-NH, 6.97 (s, 1H)
NH at1, 1.89 (s, 1H) NH at8, 0.81 (d, J ¼ 6.58 Hz, 3H) CH3 at6, 3.91
(s, 6H) OCH3. 13C NMR (ꢀ ppm): 65.006 (C7), 59.503 (C9), 40.015 (C6),
38.265 (C10), 79.285 (C5), 180.948 (C¼S), 12.124 (CH3 at6), 54.895
(OCH3), 114.383, 115.890, 128.005, 130.955, 134.746, 141.682, 157.266,
159.234 (aryl carbons). Mass (m/z): 398 (Mþ), (M.F: C21H26N4SO2), 368,
338, 323, 282, 268, 254, 239, 219, 177, 162, 148 (100%), 135, 117, 107, 75,
65, 55, 50.