E. Pomarnacka, I. Kozlarska-Kedra / Il Farmaco 58 (2003) 423ꢀ
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427
Table 4
Physico-chemical properties, analytical and spectroscopic (IR, 1H NMR) data of semicarbazides 11ꢀ
/16
No. M.p.
(8C)
Yield
(%)
Formula index (MW
)
IR (KBr, l cmꢂ1
)
1H NMR (d, ppm)
11A 216ꢀ
/
85
85
91
79
C15H13ClN4O3S2
(396.88)
3324, 3284, 3218, 1695,
1595, 1349, 1296, 1155
3324, 3284, 3218, 1695,
1595, 1349, 1296, 1155
3359, 3207, 3077, 1681,
1584, 1340, 1310, 1161
3354, 3271, 3215, 1684,
1658, 1595, 1314, 1138
2.42 (s, 3H, 7-CH3), 6.97ꢀ
1H, H-8), 8.94 (s, 1H, HN-2), 9.39 (s, 1H, HN-4), 11.23 (s, 1H, HN-1)a
2.42 (s, 3H, 7-CH3), 6.92ꢀ7.47(m, 5H, Ph), 7.97 (s, 1H, H-5), 8.0 (s,
1H, H-8), 8.85 (s, 1H, HN-1), 8.94 (s, 1H, HN-2), 9.03 (s, 1H, HN-4)a
2.51 (s, 3H, 7-CH3), 6.9ꢀ7.75 (m, 4H, Ph), 7.97 (s, 1H, H-5), 8.02 (s,
1H, H-8), 8.98 (s, 1H, HN-2), 9.42 (s, 1H, HN-4), 11,23 (s, 1H, HN-1)
6.98ꢀ7.71 (m, 10H, 2ꢃPh), 8.13 (s, 1H, H-5), 8.16 (s, 1H, H-8), 9.04
/
7.53 (m, 5H, Ph), 7.94 (s, 1H, H-5), 8.01 (s,
218
11B 216ꢀ
/
C15H13ClN4O3S2
(396.88)
/
218
12 229ꢀ
/
C15H12ClFN4O3S2
(414.87)
/
232
13 267ꢀ
/
C21H16ClN5O4S2
(501.97)
/
/
269
(s, 1H, HN-2), 9.44 (s, 1H, HN-4), 10.69 (s, 1H, NHCO), 11.39 (s, 1H,
HN-1)
14 276ꢀ
/
95
93
93
C22H18ClN5O4S2
(515.99)
3359, 3275, 3207, 1684,
1654, 1592, 1313, 1165
2.28 (s, 3H, CH3Ph), 6.98ꢀ
(s, 1H, H-8), 8.99 (s, 1H, HN-2), 9.44 (s, 1H, HN-4), 10.60 (s, 1H,
NHCO), 11.39 (s, 1H, HN-1)
/
7.61 (m, 9H, 2ꢃPh), 8.11 (s, 1H, H-5), 8.15
/
278
15 267ꢀ
/
C21H15Cl2N5O4S2
(536.42)
3359, 3256, 3201, 1684,
1657, 1592, 1352, 1305,
1163
6.97ꢀ
/
7.77 (m, 9H, 2ꢃPh), 8.17 (s, 2H, H-5, H-8), 9.0 (s, 1H, HN-2),
/
269
9.44 (s, 1H, HN-4), 10.83 (s, 1H, NHCO), 11.40 (s, 1H, HN-1)
16 255ꢀ
/
C21H15Cl2N5O4S2
(536.42)
3354, 3260, 3207, 1681,
1660, 1595, 1349, 1314,
1163
6.96ꢀ
/
7.79 (m, 9H, 2ꢃPh), 8.16 (s, 2H, H-5, H-8), 9.03 (s, 1H, HN-2),
/
257
9.45 (s, 1H, HN-4), 10.49 (s, 1H, NHCO), 11.40 (s, 1H, HN-1)
1HNMR spectra in DMSO-d6: spectrometers: 500 MHza, 200 MHz.
and analytical data were in accordance with those
reported in Table 1.
Compound 13: 13C NMR (DMSO-d6, d ppm): 119.3,
120.1, 124.7, 129.4, 129.5, 129.6, 130.3, 131.8, 132.0,
133.5, 134.0, 136.3, 136.6, 137.4 (C arom.), 154.7 (CÄ
/
N),
O semicarb.). Compound
162.8 (CÄ
/
O amide), 169.7 (CÄ
/
14: 13C NMR (DMSO-d6, d ppm): 20.64 (CH3), 119.3,
120.0, 124.5, 124.7, 129.1, 129.4, 129.6, 130.3, 131.8,
3.1.3. General procedure for preparation of 1-(6-chloro-
1,1-dioxo-7-R1-1,4,2-benzodithiazin-3-yl)-4-(R2-
132.1, 134.0, 136.6, 137.3, 138.8 (C arom.), 154.7 (CÄ
/
N),
phenyl)semicarbazides (11ꢀ
A stirred mixture of the appropriate benzodithiazine
(1ꢀ5) (15 mmol), the proper 4-arylsemicarbazide (15
/
16)
163.0 (CÄO amide), 169.7 (CÄO semicarb.).
/
/
/
mmol), and methanol (80 ml) were refluxed for 30 h
(until the evolution of CH3SH had ceased). The solid
product was filtered off, washed with methanol and
dried. Yields, melting points, analytical and spectro-
3.1.4. General procedure for preparation of 4-chloro-5-
(methyl or 4-R2-phenylcarbamoyl)-2-mercapto-N-(4,5-
dihydro-5-oxo-4-phenyl-1H-1,2,4-triazol-3-
yl)benzenesulfonamides (17ꢀ
A suspension of the appropriate semicarbazide (11ꢀ
16) (2 mmol) in 2.5% aqueous sodium hydroxide (20 ml)
/
22)
scopic data of the semicarbazides 11ꢀ16 are reported in
/
/
Table 4.
Table 5
Physico-chemical properties, IR and 1HNMR spectroscopic data of compounds 17ꢀ
/22
No. M.p.
(8C)
Yield
(%)
Formula index (MW
)
IR (KBr, l cmꢂ1
)
1H NMR (d, ppm)
17 145ꢀ
/
85
48
41
71
40
43
C15H13ClN4O3S2
(396.88)
3183, 3077, 2554, 1704, 1581,
1357, 1163
2.26 (s, 3H, 5-CH3), 7.25ꢀ
7.64 (s, 1H, H-6), 11.87 (br.s, 1H, NH)
2.35 (s, 3H, 5-CH3), 7.16ꢀ7.50 (m, 4H, Ph), 7.76 (s, 1H, H-3)
7.88 (s, 1H, H-6), 10.5 (br s, 1H, NH)
7.2ꢀ7.78(m, 10H, 2ꢃPh), 7.91 (s, 1H, H-3), 8.07 (s, 1H, H-3),
10.68 (s, 1H, NHCO)
2.30 (s, 3H, CH3), 7.12ꢀ
1H, H-6), 9.56 (br.s, 1H, NHCO)
7.08ꢀ7.87 (m, 9H, 2ꢃPh), 7.93 (s, 1H, H-3), 8.04 (s, 1H, H-6),
8.92 (s, 1H, NH), 9.85 (s, 1H, NHCO)
7.08ꢀ7.80 (m, 9H, 2ꢃPh); 8.18 (s, 1H, H-3); 8.28 (s, 1H, H-6);
9.32 (s, 1H, NHCO)
/
7.50 (m, 5H, Ph), 7.62 (s, 1H, H-3),
147
18 203ꢀ
/
C15H12ClFN4O3S2
(414.87)
3213, 3083, 2560, 1704, 1613,
1587, 1302, 1163
/
205
19 181ꢀ
/
C21H16ClN5O4S2
(501.97)
3260, 3195, 3072, 2560, 1715,
1657, 1598, 1315, 1163
3254, 3195, 3072, 2554, 1713,
1654, 1584, 1313, 1163
3254, 3195, 3054, 2554, 1716,
1660, 1595, 1307, 1163
3365, 3236, 3083, 2566, 1707,
1672, 1587, 1302, 1163
/
/
183
20 184ꢀ
/
C22H18ClN5O4S2
(515.99)
/
7.75 (m, 10H, 2ꢃPh, H-3), 8.05 (s,
/
186
21 172ꢀ
/
C21H15Cl2N5O4S2
(536.42)
/
/
175
22 160-
164
C21H15Cl2N5O4S2
(536.42)
/
/