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Mohebat et al.
1379, 1335, 1263, 1213, 1137, 1067, 766; 1H NMR (400 MHz, CDCl3): dH 7.43
(dd, 1H, J1 ¼ 7.6 Hz, J2 ¼ 1.2 Hz, Ar-H), 7.54-7.61 (m, 3H, Ar-H),7.84-7.89 (m, 2H, Ar-
H), 7.95-7.98 (m, 1H, Ar-H), 8.36-8.39 (m, 1H, Ar-H), 8.45 (d, 1H, J ¼ 8.0 Hz, Ar-H);
13C NMR (100 MHz, CDCl3): dC 118.0, 120.5, 123.1, 125.4, 126.1, 126.9, 127.0, 127.1,
128.3, 130.0, 133.1, 134.7, 145.9, 148.9, 161.3, 199.4; MS (m/z, %): 379 (Mþ, 9).
Anal. Calcd for C18H9N3O5S: C, 56.99; H, 2.39; N, 11.08; S, 8.45. Found: C,
57.12; H, 2.43; N, 11.29; S, 8.70.
2-(m-Tolyl)-4H-naphtho[2,1-e][1,3]oxazine-4-thione (5h). Yellow powder; yield
88%, 0.267 g; mp 111 ꢀC; IR (KBr) (ꢀmax, cmꢂ1): 1649, 1571, 1374, 1263, 1217, 1181,
1
1078, 762; H NMR (400 MHz, CDCl3): dH 2.39 (s, 3H, Me), 7.15 (s, 1H, Ar-H), 7.21-
7.26 (m, 1H, Ar-H), 7.34-7.44 (m, 4H, Ar-H), 7.69 (d, 1H, J ¼ 8.0 Hz, Ar-H), 7.79-7.85
(m, 1H, Ar-H), 8.06 (d, 1H, J ¼ 7.6 Hz, Ar-H), 8.21 (d, 1H, J ¼ 8.0 Hz, Ar-H); 13C
NMR (100 MHz, CDCl3): dC 21.3, 118.3, 121.3, 125.5, 126.1, 126.2, 126.4, 126.5,
127.5, 128.6, 129.2, 130.8, 131.3, 134.6, 146.9, 152.2, 165.4, 198.6; MS (m/z, %): 303
(Mþ, 23).
Anal. Calcd for C19H13NOS: C, 75.22; H, 4.32; N, 4.62; S, 10.57. Found: C, 75.11;
H, 4.50; N, 4.91; S, 10.68.
2-(o-Tolyl)-4H-naphtho[2,1-e][1,3]oxazine-4-thione (5i). Yellow powder; yield
86%, 0.261 g; mp 125-127 ꢀC; IR (KBr) (ꢀmax, cmꢂ1): 1646, 1585, 1377, 1273, 1215,
1
1149, 1076, 782; H NMR (400 MHz, CDCl3): dH 2.78 (s, 3H, Me),7.41-7.46 (m, 2H,
Ar-H), 7.55-7.58 (m, 4H, Ar-H), 7.83 (d, 1H, J ¼ 8.0 Hz, Ar-H), 7.94-8.01 (m, 2H, Ar-
H), 8.44 (d, 1H, J ¼ 7.6 Hz, Ar-H); 13C NMR (100 MHz, CDCl3): dC 22.1, 118.4,
121.3, 125.5, 126.2, 126.4, 126.5, 126.6, 127.1, 128.2, 128.8, 131.0, 131.3, 134.7,
146.9, 152.5, 165.8, 199.0; MS (m/z, %): 303 (Mþ, 14).
Anal. Calcd for C19H13NOS: C, 75.22; H, 4.32; N, 4.62; S, 10.57. Found: C, 75.39;
H, 4.45; N, 4.38; S, 10.34.
3-(3-Nitrophenyl)-1H-naphtho[1,2-e][1,3]oxazine-1-thione (6c). Pale yellow pow-
der; yield 93%, 0.311 g; mp 149-150 ꢀC; IR (KBr) (ꢀmax, cmꢂ1): 1653, 1612, 1581,
1
1527, 1344, 1294, 1156, 1056, 713; H NMR (400 MHz, CDCl3): dH 7.40 (dd, 1H,
J1 ¼ 8.8 Hz, J2 ¼ 2.4 Hz, Ar-H), 7.52-7.58 (m, 2H, Ar-H), 7.75-7.76 (m, 1H, Ar-H),
7.79 (d, 1H, J ¼ 8.0 Hz, Ar-H), 7.86-7.93 (m, 2H, Ar-H), 7.96 (d, 1H, J ¼ 8.8 Hz, Ar-
H), 8.53-8.61 (m, 2H, Ar-H); 13C NMR (100 MHz, CDCl3): dC 118.6, 120.7, 125.1,
126.0, 126.8, 127.7, 127.8, 128.0, 129.7, 129.9, 131.4, 131.7, 133.7, 135.8, 148.1,
148.4, 163.3, 199.2; MS (m/z, %): 334 (Mþ, 8).
Anal. Calcd for C18H10N2O3S: C, 64.66; H, 3.01; N, 8.38; S, 9.59. Found: C,
64.52; H, 3.14; N, 8.27; S, 9.71.
3-(3,5-Dinitrophenyl)-1H-naphtho[1,2-e][1,3]oxazine-1-thione (6d). Yellow pow-
der; yield 91%, 0.345 g; mp 172-174 ꢀC; IR (KBr) (ꢀmax, cmꢂ1): 1644, 1615, 1596,
1
1540, 1339, 1273, 1167, 1070, 756; H NMR (400 MHz, CDCl3): dH 7.40 (dd, 1H,
J1 ¼ 2.0 Hz, J2 ¼ 8.8 Hz, Ar-H), 7.54-7.60 (m, 2H, Ar-H), 7.77 (d, 1H, J ¼ 1.6 Hz, Ar-
H), 7.88-7.94 (m, 2H, Ar-H), 7.98 (d, 1H, J ¼ 8.8 Hz, Ar-H), 8.34-8.35 (m, 1H, Ar-H),
8.39 (d, 1H, J ¼ 2.0 Hz, Ar-H); 13C NMR (100 MHz, CDCl3): dC 118.5, 120.2, 122.9,
126.4, 127.0, 127.8, 127.9, 129.9, 130.0, 131.8, 133.3, 133.6, 147.7, 148.8, 161.3,
198.9; MS (m/z, %): 379 (Mþ, 10).
Anal. Calcd for C18H9N3O5S: C, 56.99; H, 2.39; N, 11.08; S, 8.45. Found: C,
57.14; H, 2.63; N, 11.25; S, 8.58.
3-(o-Tolyl)-1H-naphtho[1,2-e][1,3]oxazine-1-thione (6g). Yellow powder; yield
85%, 0.258 g; mp 127-129 ꢀC; IR (KBr) (ꢀmax, cmꢂ1): 1639, 1593, 1501, 1296, 1233,