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ACCEPTED MANUSCRIPT
cm-1. HNMR (DMSO-d6, 400 MHz): δ 11.62 (s, 1Н), 8.48 (s,
[M+H]+. Anal. Calcd for C14H17N3O: C, 69.11; H, 7.04; N, 17.27.
Found: C, 68.90; H, 7.06; N, 17.21.
1
1Н), 8.09-8.13 (m, 2Н), 7.92 (d, J= 9 Hz, 1Н), 7.64 (d, J= 6 Hz,
1Н), 7.59 (m, 3Н), 7.55 (t, J= 3.0 Hz, 1Н), 6.68 (s, 1Н). 13СNMR
(DMSO-d6, 100 MHz): δ 177.1, 168.1, 138.5, 131.5, 129.2,
127.9, 127.1, 126.7, 121.3, 120.6, 114.3, 112.5, 102.8. MS
(ESI+): m/z 262 [M+H]+. Anal. Calcd for C16H11N3O: C, 73.55;
H, 4.24; N, 16.08. Found: C, 73.33; H, 4.25; N, 16.03.
3-(4-Methylphenyl)-1,2,4-oxadiazol-5(4H)-one17g (3ac). White
solid; yield: 82% (289 mg); mp 217-218 °C (lit.17g mp 222-
224 °C). IR (neat): 3129, 3048, 1761, 1740, 1608, 1552, 1462,
1256, 999, 951, 885, 820, 743 cm-1. H NMR (DMSO-d6, 400
1
MHz): δ 12.82 (br. s, 1H), 7.69 (d, J = 8.1 Hz, 2Н), 7.37 (d, J =
5-(1-Methyl-1H-pyrrol-2-yl)-3-phenyl-1,2,4-oxadiazole (3x).
Yellow pale solid, yield: 69% (310 mg); mp 98-99 °C. IR (neat):
1605, 1526, 1447, 1406, 1361, 1246, 1126, 1059, 914, 739, 694
7.8 Hz, 2Н), 2.37 (s, 3Н). MS (ESI+): m/z 177 [M+H]+.
1
cm-1. H NMR (DMSO-d6, 400 MHz): δ 8.08 (m, 2H), 7.56-7.60
tert-Butyl-4-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-
(m, 3H), 7.29 (s, 1H), 7.11 (dd, J1= 3.9 Hz, J2= 1.5 Hz, 1H),
6.27-6.29(dd, J1= 3.6 Hz, J2= 2.4 Hz, 1H), 4.07 (s, 3H).13С NMR
(DMSO-d6, 100 MHz): δ 169.5, 167.5, 139.3, 131.5, 130.8,
129.2, 127.1, 126.4, 116.9, 116.6, 109.4, 36.5.MS (ESI+): m/z
226 [M+H]+. Anal. Calcd for C13H11N3O: C, 69.32; H, 4.92; N,
18.66. Found: C, 69.11; H, 4.93; N, 18.59.
yl]piperidine-1-carboxylate (3ad). White solid; yield: 88% (604
mg); mp 87-88 °C. IR (neat): 1690, 1585, 1562, 1402, 1361,
1228, 1159, 1114, 1034, 831, 743 cm-1. 1H NMR (DMSO-d6, 400
MHz): δ 7.89 (d, J = 8.8 Hz, 2Н), 7.36 (d, J = 8.8 Hz, 2Н), 3,95
(br d, J = 15 Hz), 3.28-3.35(m, 1H), 2.97 (t, J = 9 Hz, 1Н), 2.37
(s, 3H), 2.04-2.09 (dd, J1= 12,1 Hz, J2= 3,0 Hz, 2Н), 1.59-1.73
(m, 2Н), 1.39(s, 1H). 13С NMR (DMSO-d6, 100 MHz): δ 181.1,
167.5, 153.9, 141.5, 129.8, 127.0, 123.6, 78.9, 40.5, 33.4, 28.8,
28.1, 21.1. MS (ESI+): m/z 344 [M+H]+. Anal. Calcd for
C19H25N3O3: C, 66.45; H, 7.34; N, 12.24. Found: C, 66.25; H,
7.35; N, 12.19.
3-(Pyridin-2-yl)-5-(4-methylphenyl)-1,2,4-oxadiazole
(3y).
White solid; yield: 87% (413 mg); mp 110-111 °C. IR (neat):
1612, 1587, 1562, 1499, 1412, 1364, 1157, 829, 805, 740, 714
cm-1.1H NMR (DMSO-d6, 400 MHz): δ 8.77 (d, J = 3.9 Hz, 1H),
8.15 (d, J = 7.5 Hz, 1H), 8.01-8.06 (m, 3H), 7.60-7.64 (m, 1H),
7.57 (d, J = 8.1 Hz, 2H), 2.41 (s, 3H). 13С NMR (DMSO-d6, 100
MHz): δ 175.8, 168.3, 150.3, 145.8, 143.9, 137.7, 130.2, 127.9,
126.2, 123.5, 120.7, 21.3. MS (ESI+): m/z 238 [M+H]+. Anal.
Calcd for C14H11N3O: C, 70.87; H, 4.67; N, 17.71. Found: C,
70.66; H, 4.68; N, 17.65.
Acknowledgements
This paper was financially supported by the Ministry of
Education and Science of the Russian Federation on the program
to improve the competitiveness of People’s Friendship University
(RUDN University) among the world’s leading research and
education centers in the 2016-2020 (the Agreement number
02.a03.21.0008).
5-(Pyridin-2-yl)-3-(4-methylphenyl)-1,2,4-oxadiazole
(3z).
White solid; yield: 79% (375 mg); mp 96-97 °C. IR (neat): 1612,
1589, 1562, 1479, 1414, 1360, 1138, 829, 741, 719 cm-1. 1H
NMR (DMSO-d6, 400 MHz): δ 8.82 (d, J = 4.4 Hz, 1H), 8.28 (d,
J = 7.8 Hz, 1H), 8.07-8.12 (m, 1H), 7.96 (d, J = 8.1 Hz, 2H), 7.70
(m, 1H), 7.37 (d, J = 8.1 Hz, 2H), 2.37 (s, 3H). 13С NMR
(DMSO-d6, 100 MHz): δ 174.3, 168.4, 150.6, 142.9, 141.7,
138.1, 129.8, 127.4, 127.1, 124.5, 123.3, 21.2. MS (ESI+): m/z
238 [M+H]+. Anal. Calcd for C14H11N3O: C, 70.87; H, 4.67; N,
17.71. Found: C, 70.65; H, 4.69; N, 17.66.
References and notes
1. Pace, A.; Buscemi, S.; Piccionello, A. P.; Pibiri, I. Adv Heterocyc.
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2016, 26, 645. (b) Shruthi, N.; Poojary, B.; Kumar, V.; Hussain,
M. M.; Rai, V. M.; Pai, V. R.; Bhat, M.; Revannasiddappa, B .C.
RSC Adv. 2016, 6, 8303. (c) Spink, E.; Ding, D.; Peng, Z.;
Boudreau, M. A.; Leemans, E.; Lastochkin, E.; Song, W.;
Lichtenwalter, K.; O’Daniel, P. I.; Testero, S. A.; Pi, H.;
Schroeder, V. A.; Wolter, W. R.; Antunes, N. T.; Suckow, M. A.;
Vakulenko, S.; Chang, M.; Mobashery, S. J Med Chem. 2015, 58,
1380. (d) O’Daniel, P. I.; Peng, Z.; Pi, H.; Testero, S. A.; Ding, D.;
Spink, E.; Leemans, E.; Boudreau, M. A.; Yamaguchi, T.;
Schroeder, V. A.; Wolter, W. R.; Llarrull, L. I.; Song, W.;
Lastochkin, E.; Kumarasiri, M;, Antunes, N. T.; Espahbodi, M.;
Lichtenwalter, K.; Suckow, M. A.; Vakulenko, S.; Mobashery, S.;
Chang, M. J Am Chem Soc. 2014, 136, 3664.
3. (a) Khan, I.; Ibrar, A.; Abbas, N. Arch Pharm Chem Life Sci.
2013, 347, 1. (b) Rubino, S.; Pibiri, I.; Costantino, C.; Buscemi,
S.; Girasolo, M. A.; Attanzio, A.; Tesoriere, L. J Inorg Biochem.
2016, 155, 92.
4. (a) Bokor, E.; Szennyes, E.; Csupasz, T.; Toth, N.; Docsa, T.;
Gergely, P.; Somsák, L. Carbohydrate Research 2015, 412, 71. (b)
Quattropani, A.; Sauer, W. H. B.; Crosignani, S.; Dorbais, J.;
Gerber, P.; Gonzalez, J.; Marin, D.; Muzerelle, M.; Beltran, F.;
Nichols, A.; Georgi, K.; Schneider, M.; Vitte, P. A.; Eligert, V.;
Novo-Perez, L.; Hantson, J.; Nock, S.; Carboni, S.; de Souza, A.
L. S.; Arrighi, J. F.; Boschert, U.; Bombrun, A. ChemMedChem
2015, 10, 688. (c) Cao, Y.; Min, C.; Acharya, S.; Kim, K. M.;
Cheon, S. H. Bioorg Med Chem. 2016, 24, 191.
[3-(4-Methylphenyl)-1,2,4-oxadiazol-5-yl]methanol17f (3aa).
White solid; yield: 70% (266 mg); mp 84-85 °C (lit.17f mp 84-
85 °C). IR (neat): 1589, 1485, 1344, 1248, 1083, 893, 829, 738
cm-1. 1H NMR (DMSO-d6, 400 MHz): δ 7.90 (d, J = 7.8 Hz, 2Н),
7.36 (d, J = 7.8 Hz, 2Н), 6.05 (t, J = 6.2 Hz, 1Н), 4.79 (d, J = 6.1
Hz, 2Н), 2.37 (s, 3H). 13С NMR (DMSO-d6, 100 MHz): δ 179.4,
167.5, 141.6, 129.9, 127.0, 123.5, 55.2, 21.1. MS (ESI+): m/z 191
[M+H]+.
5-(Piperidin-4-yl)-3-(4-methylphenyl)-1,2,4-oxadiazole (3ab).
White solid; yield: 30% (146 mg); mp 82-83 °C. IR (neat): 3252,
2951, 1634, 1564, 1412, 1348, 1258, 1114, 1001, 823, 741 cm-1.
1H NMR (DMSO-d6, 400 MHz): δ 7.88 (d, J = 8.1 Hz, 2Н), 7.34
(d, J = 8.1 Hz, 2Н), 3.25 (s, 1H), 3.11-3.19 (m, 1H), 2.98 (br. s,
2H), 2.61 (m, 2Н), 2.36 (s, 3H), 1.94-1.98 (m, 2H), 1.61-1.71 (m,
2H). 13С NMR (DMSO-d6, 100 MHz): δ 182.4, 167.4, 141.4,
129.8, 127.0, 123.7, 45.0, 34.3, 30.0, 21.1.MS (ESI+): m/z 244
5. (a) Subrao, M.; Potukuchi, D. M.; Sharada Ramachandra, G.;