154
S. Saravanan, A. Nithya and S. Muthusubramanian
Vol. 43
-1
1
m/z 344 (0.1%), 296 (13%), 281 (3%). 255 (100%), 239 (4%),
212 (6%), 202 (7%), 189 (4%), 91 (2%), 77 (2%).
(potassium bromide): 2994, 2927, 1541, 1452, 1338 cm ;
H
NMR: δ 1.55 (s, 6H), 5.36 (s, 1H), 7.14-7.17 (m, 2H), 7.32-7.35
(m, 3H), 7.40-7.43 (m, 2H), 7.51-7.54 (m, 3H); C NMR: 23.8,
13
Anal. Calcd. for C H ClN O Se: C, 50.62; H, 4.02; N, 9.32.
19 18 3 3
25.5, 55.8, 91.0, 128.4, 128.8, 129.0, 129.3, 129.9, 130.0, 131.7,
135.1, 155.0, 162.9; ms: m/z 249 (1%), 232 (24%), 217 (26%),
202 (21%), 191 (100%), 189 (33%), 91 (56%), 77 (25%).
Found: C, 50.69; H, 4.10; N, 9.41.
4-(4-Chlorophenyl)-5-[1-(4-chlorophenyl)-2-methyl-2-nitro-
propyl]-1,2,3-selenadiazole (4f).
Anal. Calcd. for C
H N O Se: C, 55.96; H, 4.44; N, 10.88.
18 17 3 2
This compound was obtained as colourless crystals (ethanol),
reaction time 2 hrs, yield 71 %, mp 148-149 ºC; ir (potassium
Found: C, 56.16; H, 4.64; N, 11.02.
5-[2-Methyl-1-(4-methylphenyl)-2-nitropropyl]-4-phenyl-1,2,3-
selenadiazole (4b).
-1
1
bromide): 2981, 2933, 1541, 1340, 1086 cm ; H NMR: δ 1.56
(s, 3H), 1.57 (s, 3H), 5.27 (s, 1H), 7.08 (d, J = 8.4 Hz, 2H), 7.31-
13
7.35 (m, 4H), 7.51 (d, J = 8.4 Hz, 2H); C NMR: 23.6, 25.6,
This compound was obtained as colourless crystals (ethanol),
reaction time 2 hrs, yield 65 %, mp 96 ºC; ir (potassium bro-
55.2, 90.7, 129.2, 129.4, 130.0, 131.2, 131.3, 133.3, 134.8, 135.7,
154.8, 161.7; ms: m/z 347 (0.1%), 302 (62%), 282 (17%), 266
(31%), 259 (100%), 223 (31%), 215 (88%), 189 (61%), 94
(36%), 77. (8%).
-1
1
mide): 2989, 2927, 1541, 1456, 1342 cm ; H NMR: δ 1.54 (s,
3H), 1.55 (s, 3H), 2.33 (s, 3H), 5.32 (s, 1H), 7.04 (d, J = 8.4 Hz,
2H), 7.14 (d, J = 8.4 Hz, 2H), 7.41-7.45 (m, 2H), 7.51-7.54 (m,
13
Anal. Calcd. for C
H Cl N O Se: C, 47.49; H, 3.32; N,
3H); C NMR: 21.0, 23.9, 25.3, 55.4, 91.1, 128.8, 129.2, 129.7,
18 15 2 3 2
9.23. Found: C, 47.55; H, 3.38; N, 9.32.
129.8, 130.0, 131.8, 132.0, 138.4, 155.2, 162.7; ms: m/z 263
(1%), 246 (23%), 231 (12%), 215 (15%), 205 (100%), 202
(23%), 189 (10%), 91 (15%), 77 (14%).
5-[2-Methyl-1-(4-methylphenyl)-2-nitropropyl]-4-(4-methyl-
phenyl)-1,2,3-selenadiazole (4g).
Anal. Calcd. for C
H N O Se: C, 57.00; H, 4.78; N, 10.50.
19 19 3 2
This compound was obtained as colourless crystals (ethanol),
reaction time 2 hrs, yield 64 %, mp 94-95 ºC; ir (potassium bro-
Found: C, 57.21; H, 4.82; N, 10.63.
5-[1-(4-Methoxyphenyl)-2-methyl-2-nitropropyl]-4-phenyl-
1,2,3-selenadiazole (4c).
-1
1
mide): 2919, 1541, 1342, 1024 cm ; H NMR: δ 1.53 (s, 3H),
1.55 (s, 3H), 2.33 (s, 3H), 2.47 (s, 3H), 5.33 (s, 1H), 7.05 (d, J =
13
7.8 Hz, 2H), 7.15 (d, J = 7.8 Hz, 2H), 7.32 (s, 4H); C NMR:
This compound was obtained as colourless crystals (ethanol),
reaction time 2 hrs, yield 69 %, mp 82-83 ºC; ir (potassium bro-
21.0, 21.4, 24.0, 25.2, 55.4, 91.1, 128.8, 129.5, 129.7, 129.8,
129.9, 132.1, 138.3, 139.2, 154.8, 162.9; ms: m/z 260 (16%), 245
(14%), 230 (11%), 219 (100%), 202 (22%), 185 (20%), 91
(17%), 77 (12%).
-1
1
mide): 2989, 2933, 1541, 1460, 1346 cm ; H NMR: δ 1.54 (s,
3H), 1.55 (s, 3H), 3.79 (s, 3H), 5.30 (s, 1H), 6.86 (d, J = 9.0 Hz,
2H), 7.07 (d, J = 9.0 Hz, 2H), 7.41-7.44 (m, 2H), 7.51-7.54 (m,
13
Anal. Calcd. for C
H N O Se: C, 57.97; H, 5.11; N, 10.14.
3H); C NMR: 23.8, 25.3, 55.0, 55.3, 91.1, 114.3, 126.8, 128.8,
20 21 3 2
Found: C, 58.04; H, 5.18; N, 10.22.
129.2, 129.9, 131.0, 131.8, 155.3, 159.4, 162.6; ms: m/z 309
(0.1%), 279 (0.1%), 262 (13%), 247 (5%), 232 (2%), 221
(100%), 202 (5%), 189 (4%), 91 (5%), 77 (4%).
5-[1-(4-Methoxyphenyl)-2-methyl-2-nitropropyl]-4-(4-methyl-
phenyl)-1,2,3-selenadiazole (4h).
Anal. Calcd. for C
H N O Se: C, 54.81; H, 4.60; N, 10.09.
19 19 3 3
This compound was obtained as colourless crystals (ethanol),
reaction time 2 hrs, yield 67 %, mp 141-142 ºC; ir (potassium
bromide): 2979, 2927, 1537, 1462, 1342 cm ; H NMR: δ 1.53
(s, 3H), 1.55 (s, 3H), 2.47 (s, 3H), 3.79 (s, 3H), 5.31 (s, 1H), 6.86
Found: C, 54.78; H, 4.65; N, 10.15.
4-(4-Chlorophenyl)-5-[2-methyl-1-(4-methylphenyl)-2-nitro-
propyl]-1,2,3-selenadiazole (4d).
-1
1
13
(d, J = 8.7 Hz, 2H), 7.08 (d, J = 8.7 Hz, 2H), 7.32 (s, 4H);
C
This compound was obtained as colourless crystals (ethanol),
reaction time 2 hrs, yield 67 %, mp 133-134 ºC; ir (potassium
NMR: 21.4, 24.0, 25.1, 55.1, 55.3, 91.2, 114.3, 127.0, 128.8,
129.5, 129.8, 131.1, 139.2, 154.9, 159.4, 162.7; ms: m/z 276
(12%), 261 (6%), 246 (3%), 235 (100%), 219 (2%), 202 (3%),
189 (6%), 91 (8%), 77 (8%).
-1
1
bromide): 2990, 2931, 1537, 1458, 1342 cm ; H NMR: δ 1.55
(s, 3H), 1.57 (s, 3H), 2.33 (s, 3H), 5.27 (s, 1H), 7.04 (d, J = 8.1
Hz, 2H), 7.16 (d, J = 8.1 Hz, 2H), 7.36 (d, J = 8.4 Hz, 2H), 7.50
13
*
Anal. Calcd. for C
H N O Se: C, 55.82; H, 4.92; N, 9.76.
(d, J = 8.4 Hz, 2H); C NMR : 21.0, 23.3, 25.8, 55.5, 91.0,
129.1, 129.8, 130.2, 131.4, 131.7, 135.4, 138.5, 155.6, 161.5; ms:
m/z 328 (0.1%), 296(0.4%), 281 (25%), 239 (100%), 215 (27%),
202 (34%), 189 (11%), 91 (11%), 77 (12%) (one aromatic carbon
resonance is merged with another).
20 21 3 3
Found: C, 55.89; H, 4.89; N, 9.84.
4-[1,1'-Biphenyl]-4-yl-5-[1-(4-methoxyphenyl)-2-methyl-2-
nitropropyl]-1,2,3-selenadiazole (4i).
This compound was obtained as colourless crystals (ethanol),
reaction time 2 hrs, yield 66 %, mp 128-130 ºC; ir (potassium bro-
Anal. Calcd. for C
H ClN O Se: C, 59.49; H, 4.17; N, 9.66.
19 18 3 2
Found: C, 59.54; H, 4.25; N, 9.75.
-1
1
mide): 2993, 2927, 1541, 1473, 1338 cm ; H NMR: δ 1.57 (s,
3H), 1.58 (s, 3H), 3.80 (s, 3H), 5.37 (s, 1H), 6.88 (d, J = 8.7 Hz, 2H),
7.11 (d, J = 8.7 Hz, 2H), 7.41 (tt, J = 8.1, 2.1 Hz, 1H), 7.49 (d, J =
8.1 Hz, 2H), 7.51 (d, J = 8.1 Hz, 2H), 7.71 (d, J = 8.7 Hz, 2H), 7.76
4-(4-Chlorophenyl)-5-[1-(4-methoxyphenyl)-2-methyl-2-nitro-
propyl]-1,2,3-selenadiazole (4e).
This compound was obtained as colourless crystals (ethanol),
reaction time 2 hrs, yield 73 %, mp 121-122 ºC; ir (potassium
13
(d, J = 8.7 Hz, 2H); C NMR: 23.8, 25.4, 55.1, 55.3, 91.2, 114.4,
-1
1
126.9, 127.2, 127.5, 127.8, 128.9, 130.4, 130.7, 131.1, 140.3, 142.0,
155.2, 159.4, 162.4; ms: m/z 493 (0.1%), 385 (0.1%), 338 (28%),
323 (7%), 297 (100%), 252 (16%), 201 (10%), 77 (2%).
bromide): 2987, 2930, 1539, 1460, 1346 cm ; H NMR: δ 1.55
(s, 3H), 1.56 (s, 3H), 3.80 (s, 3H), 5.25 (s, 1H), 6.87 (d, J = 8.7
Hz, 2H), 7.07 (d, J = 8.7 Hz, 2H), 7.36 (d, J = 8.7 Hz, 2H), 7.50
13
Anal. Calcd. for C
H N O Se: C, 60.98; H, 4.71; N, 8.53.
(d, J = 8.7 Hz, 2H); C NMR: 23.4, 25.7, 55.1, 55.3, 91.1, 114.5,
25 23 3 3
Found: C, 61.13; H, 4.49; N, 8.55.
126.6, 129.1, 130.3, 131.1, 131.3, 135.5, 155.7, 159.5, 161.4; ms: