Mendeleev Commun., 2016, 26, 264–265
3 V. N. Yarovenko, V. Z. Shirinyan, I. V. Zavarzin and M. M. Krayushkin,
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V. N. Yarovenko, I. V. Zavarzin and M. M. Krayushkin, Bull. Acad. Sci.
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986, 1213).
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V. N. Yarovenko, V. K. Taralashvili, I. V. Zavarzin and M. M. Krayushkin,
5
6
Tetrahedron, 1990, 46, 3941.
5
-Methyl-3-(4-nitrophenyl)-1,2,4-oxadiazole 2c. Yield 68%, mp 142–143°C
lit., 143–145°C). H NMR (500 MHz, DMSO-d ) d: 2.72 (s, 3H, Me),
.23 (d, 2H, Ar, J 8.7 Hz), 8.38 (d, 2H, Ar, J 8.7 Hz). C NMR (125 MHz,
DMSO-d ) d: 12.1, 124.4, 128.3, 132.1, 149.1, 166.4, 178.3. MS (EI),
1
0
1
(
8
6
13
6
+
7 D. I. Moskvin and A. A. Zharov, in Sintezy organicheskikh soedinenii
Syntheses of Organic Compounds), ed. M. P. Egorov, N. D. Zelinsky
m/z: 205 (M , 100), 175 (36), 164 (79), 159 (8), 147 (10), 134 (48), 117
(
(
15), 106 (39), 90 (19), 88 (48), 87 (8), 76 (19), 75 (17), 62 (21), 51 (16).
11
Institute of Organic Chemistry, Moscow, 2008, vol. 3, pp. 175–178 (in
Russian).
R. Tadikonda and N. Ramu, Synth. Commun., 2014, 44, 1978.
S. Chiou, A. K. M. M. Hoque and H. J. Shine, J. Org. Chem., 1990, 55,
3
,5-Diphenyl-1,2,4-oxadiazole 3a. Yield 19%, mp 109–110°C (lit.,
1
1
7
03–105°C). H NMR (500 MHz, DMSO-d ) d: 7.63 (t, 2H, Ar, J 7.5 Hz),
.68 (t, 2H, Ar, J 7.5 Hz), 7.75 (t, 2H, Ar, J 7.5 Hz), 8.11 (d, 2H, Ar,
J 8.0 Hz), 8.20 (d, 2H, Ar, J 8.6 Hz). C NMR (125 MHz, DMSO-d6)
d: 123.4, 126.2, 127.1, 127.9, 129.3, 129.6, 131.6, 133.4, 168.3, 175.5.
MS (EI), m/z: 222 (M , 56), 119 (100), 111 (5), 105 (6), 96 (7), 91 (23),
7 (23), 64 (18), 51 (18).
5-Bis(4-methoxyphenyl)-1,2,4-oxadiazole 3b. Yield 20%, mp 126–127°C
lit., 126–128°C). H NMR (500 MHz, DMSO-d ) d: 3.86 (s, 3H, OMe),
.88 (s, 3H, OMe), 7.12 (d, 2H, Ar, J 8.6 Hz), 7.18 (d, 2H, Ar, J 8.7 Hz),
.01 (d, 2H, Ar, J 8.6 Hz), 8.10 (d, 2H, Ar, J 8.7 Hz). 13C NMR (125 MHz,
DMSO-d ) d: 55.4, 55.6, 114.6, 114.9, 115.9, 118.6, 128.8, 129.9, 161.7,
6
8
9
13
3
227.
1
1
0 D. N. Nicolaides, K. E. Litinas, I. Vrasidas and K. C. Fylaktakidou,
J. Heterocycl. Chem., 2004, 41, 499.
1 O. Hiromichi, I. Junya, T. Daisuke and T. Masanori, Tetrahedron Lett.,
+
7
3
,
2
014, 55, 979.
12
1
(
3
8
6
12 R. Shahnaz, G. Hamid Reza, A. Reza and A. Ali-Mohammad, Synth.
Commun., 2010, 40, 3084.
13 O. M. Lebrini, M. Lagrenée and M. Bentiss, J. Heterocycl. Chem., 2007,
44, 1529.
6
+
1
63.0, 167.8, 175.0. MS (EI), m/z: 282 (M , 100), 149 (6), 134 (6), 133 (7),
14 A. Herrera, R. Martínez-Alvarez, P. Ramiro, M. Chioua and R. Chioua,
1
19 (6), 106 (6), 92 (5), 76 (8), 63 (8), 50 (6).
Synthesis, 2004, 503.
3
,5-Bis(4-nitrophenyl)-1,2,4-oxadiazole 3c.Yield 20%, mp 235–236°C
lit., 238–240°C). 1H NMR (500 MHz, DMSO-d ) d: 8.29 (d, 2H,
1
3
(
6
13
Ar, J 8.8 Hz), 8.38–8.51 (m, 4H, Ar), 8.43 (d, 2H, Ar, J 9 Hz). C NMR
(
125 MHz, DMSO-d ) d: 124.5, 124.6, 128.3, 128.5, 129.5, 131.4, 149.3,
6
+
1
1
6
50.1, 167.2, 174.4. MS (EI), m/z: 312 (M , 24), 282 (4), 164 (20), 150 (7),
34 (15), 116 (9), 105 (12), 104 (13), 102 (11), 90 (7), 88 (14), 76 (38),
2 (14), 50 (20), 30 (100).
2
,4,6-Trimethyl-1,3,5-triazine 4. Yield 26%, mp 54–56 °C (lit.,14
1
5
4–56°C). H NMR (300 MHz, DMSO-d ) d: 2.43 (s, 9H, Me). MS (EI),
6
+
m/z: 123 (M , 88), 103 (43), 96 (18), 85 (52), 83 (100), 76 (15), 67 (8),
6
6 (8), 47 (18).
Received: 14th October 2015; Com. 15/4751
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