Journal of the Iranian Chemical Society
(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl piperi-
dine-1-carbodithioate (6d) Pale brown solid; yield 80%;
m.p. 151–156 °C, IR (KBr, cm−1) νmax 3329, 3015, 2859,
1653, 1546, 1474, 1449, 1380, 1297, 1245, 1219, 1171,
1117, 972, 839, 740; 1H NMR (300 MHz, CDCl3) δ (ppm):
9.8 (br, 1H), 5.89 (s, 1H), 4.49 (s, 2H), 4.13 (t, J=6.6 Hz,
2H), 3.84 (t, J = 6.6 Hz, 2H), 2.20 (s, 3H), 1.23–1.28 (m,
6H); 13C NMR (75 MHz, CDCl3) δ (ppm): 192.5, 164.9,
164.2, 160.1, 101.1, 99.7, 52.7, 51.3, 31.8, 26.2, 25.5, 24.4,
19.4. Anal. calcd for C13H17NO3S2: C 52.15, H 5.71, N 4.68.
Found: C 52.03, H 5.82, N 4.65.
(dt, J=1.0, J=8.1 Hz, 1H), 7.16 (d, J=8.9 Hz, 1H), 5.19
(s, 2H), 4.09 (q, J=7.09 Hz, 2H), 3.76 (q, J=7.09 Hz, 2H),
1.28 (m, 6H); 13C NMR (75 MHz, CDCl3) δ (ppm): 195.5,
152.7, 132.7, 129.5, 128.7, 128.4, 122.7, 121.8, 119.1,
114.2, 46.9, 33.1, 11.9, 11.1. Anal. calcd for C16H19NOS2:
C 62.91, H 6.25, N 4.59. Found: C 62.83, H 6.34, N 4.57.
(2-Hydroxynaphthalen-1-yl)methyl diethylcarbamodithio-
ate (8b) Off-white solid; yield 84%; m.p. 130–132 °C, IR
(KBr, cm−1) νmax 3281, 3056, 2975, 2930, 1626, 1581, 1492,
1452, 1422, 1223, 1202, 1143, 1122, 1062, 973, 914, 862,
1
811, 747; H NMR (300 MHz, CDCl3) δ (ppm): 8.25 (s,
(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl morpho-
line-4-carbodithioate (6e) Pale brown solid; yield 70%;
m.p. 130–133 °C, IR (KBr, cm−1) νmax 3291, 3015, 1653,
1589, 1509, 1476, 1350, 1297, 1234, 1208, 1125, 1104, 979,
1H),7.81 (d, J=8.1 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.69
(d, J=8.9 Hz, 1H), 7.53 (dt, J=1.0, J=8.1 Hz, 1H), 7.36
(dt, J=1.0, J=8.1 Hz, 1H), 7.16 (d, J=8.9 Hz, 1H), 5.19
(s, 2H), 4.09 (q, J=7.09 Hz, 2H), 3.76 (q, J=7.09 Hz, 2H),
1.28 (m, 6H); 13C NMR (75 MHz, CDCl3) δ (ppm): 195.5,
152.7, 132.7, 129.5, 128.7, 128.4, 122.7, 121.8, 119.1,
114.2, 46.9, 33.1, 11.9, 11.1. Anal. calcd for C16H19NOS2:
C 62.91, H 6.25, N 4.59. Found: C 62.83, H 6.34, N 4.57.
1
820, 715; H NMR (300 MHz, CDCl3) δ (ppm): 9.20 (br,
1H), 5.85 (s, 1H), 4.63 (s, 2H), 4.35 (t, J = 6.4 Hz, 2H),
4.10 (t, J = 6.4 Hz, 2H), 3.63 (m, 4H), 2.47 (s, 3H); 13C
NMR (75 MHz, CDCl3) δ (ppm): 199.1, 166.8, 164.9, 161.0,
101.2, 99.7, 66.2, 65.4, 52.4, 50.5, 32.3, 19.9. Anal. calcd
for C12H15NO4S2: C 47.82, H 5.02, N 4.65. Found: C 47.75,
H 5.12, N 4.62.
(2-Hydroxynaphthalen-1-yl)methyl dimethylcarbamodithio-
ate (8c) Off-white solid; yield 90%; m.p. 145–148 °C, IR
(KBr, cm−1) νmax 3172, 2869, 1652, 1603, 1589, 1426, 1380,
1
(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl
azepane-1-carbodithioate (6f) Pale brown solid; yield 78%;
1209, 1119, 921, 817, 775; H NMR (300 MHz, CDCl3)
δ (ppm): 9.55 (s, 1H), 7.85 (m, 2H), 7.32–7.45 (m, 3H),
7.32 (d, J=7.1 Hz, 1H), 5.19 (s, 2H), 3.57 (s, 3H), 3.44 (s,
3H); 13C NMR (75 MHz, CDCl3) δ (ppm): 192.8, 153.9,
135.2, 130.3, 128.9, 128.5, 122.7, 122.1, 119.3, 114.5, 56.5,
34.2. Anal. calcd for C14H15NOS2: C 60.63, H 5.43, N 5.05.
Found: C 60.51, H 5.51, N 5.02.
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m.p. 153–155 °C, H NMR (300 MHz, CDCl3) δ (ppm):
8.70 (br, 1H), 5.80 (s, 1H), 4.53 (s, 2H), 4.20 (t, J=6.1 Hz,
2H), 3.90 (t, J=6.1 Hz, 2H), 2.17 (s, 3H), 1.85 (m, 4H), 1.54
(m, 4H); 13C NMR (75 MHz, CDCl3) δ (ppm): 194.7, 167.8,
165.3, 161.6, 101.7, 101.3, 56.2, 52.1, 30.5, 28.2, 27.8, 26.9,
26.5, 19.5. Anal. calcd for C14H19NO3S2: C 53.64, H 6.12,
N 4.47. Found: C 53.51, H 6.19, N 4.45.
(2-Hydroxynaphthalen-1-yl)methyl piperidine-1-carbod-
ithioate (8d) Off-white solid; yield 80%; m.p. 137–139 °C,
IR (KBr, cm−1) νmax 3301, 3117, 2986, 1617, 1589, 1486,
(2-Hydroxynaphthalen-1-yl)methyl pyrrolidine-1-carbodith-
ioate (8a) Off-white solid; yield 96%; m.p. 136–138 °C, IR
(KBr, cm−1) νmax 3276, 2987, 2860, 1631, 1603, 1513, 1492,
1450, 1352, 1239, 1157, 1002, 919, 862, 835, 743; 1H NMR
(300 MHz, CDCl3) δ (ppm): 8.50 (br, 1H), 7.79 (m, 2H),
7.26–7.31 (m, 3H), 7.25 (d, J=7.9 Hz, 1H), 5.21 (s, 2H),
4.00 (t, J=6.6 Hz, 2H), 3.64 (t, J=6.6 Hz, 2H), 1.91–2.12
(m, 4H); 13C NMR (75 MHz, CDCl3) δ (ppm): 197.5, 154.7,
135.1, 130.2, 129.8, 128.8, 122.9, 122.1, 119.7, 114.8, 54.9,
50.6, 33.3, 26.5, 24.6. Anal. calcd for C16H17NOS2: C 63.33,
H 5.65, N 4.62. Found: C 63.20, H 5.72, N 4.61.
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1459, 1422, 1223, 1219, 1143, 1131, 832, 715; H NMR
(300 MHz, CDCl3) δ (ppm): 9.55 (s, 1H), 7.85 (m, 2H),
7.32–7.45 (m, 3H), 7.32 (d, J =7.1 Hz, 1H), 5.21 (s, 2H),
4.12 (t, J= 6.0 Hz, 2H), 3.52 (t, J= 6.0 Hz, 2H), 1.62 (m,
6H);13C NMR (75 MHz, CDCl3) δ (ppm): 194.5, 154.5,
135.0, 130.4, 129.7, 128.4, 122.7, 122.0, 119.9, 114.5, 52.9,
51.6, 33.6, 26.5, 25.0, 24.8. Anal. calcd for C17H19NOS2:
C 64.32, H 6.02, N 4.41. Found: C 64.27, H 6.12, N 4.39.
(2-Hydroxynaphthalen-1-yl)methyl morpholine-4-carbodith-
ioate (8e) Off-white solid; yield 75%; m.p. 123–125 °C, IR
(KBr, cm−1) νmax 3321, 3079, 2968, 1603, 1543, 1465, 1474,
1441,1216, 1158, 1112, 950, 853, 749; 1H NMR (300 MHz,
CDCl3) δ (ppm): 9.10 (br, 1H), 7.72–7.84 (m, 2H), 7.68
(d, J = 8.8 Hz, 1H), 7.45 (m, 1H), 7.29 (m, 1H), 7.10 (d,
J=8.8 Hz, 1H), 5.20 (s, 2H), 4.16 (m, 4H), 3.91 (m, 4H);
13C NMR (75 MHz, CDCl3) δ (ppm): 197.1, 153.0, 134.7,
130.4, 128.9, 128.5, 123.9, 122.5, 121.3, 115.8, 67.1, 66.0,
(2-Hydroxynaphthalen-1-yl)methyl diethylcarbamodithio-
ate (8b) Off-white solid; yield 84%; m.p. 130–132 °C, IR
(KBr, cm−1) νmax 3281, 3056, 2975, 2930, 1626, 1581, 1492,
1452, 1422, 1223, 1202, 1143, 1122, 1062, 973, 914, 862,
1
811, 747; H NMR (300 MHz, CDCl3) δ (ppm): 8.25 (s,
1H),7.81 (d, J=8.1 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.69
(d, J=8.9 Hz, 1H), 7.53 (dt, J=1.0, J=8.1 Hz, 1H), 7.36
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