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G. Zhang et al.
Letter
Synlett
References and Notes
(5) (a) Guin, S.; Tuhin, G.; Rout, S. K.; Banerjee, A.; Patel, B. K. Org.
Lett. 2011, 13, 5976. (b) Jiang, H.; Li, X.; Pan, X.; Zhou, P. Pure
Appl. Chem. 2011, 84, 553. (c) Yadav, A. K.; Yadav, L. D. S. Tetra-
hedron Lett. 2014, 55, 2065.
(6) Kawano, T.; Yoshizumi, T.; Hirano, K.; Satoh, T.; Miura, M. Org.
Lett. 2009, 11, 3072.
(1) (a) Yale, H. L.; Losee, K. J. Med. Chem. 1966, 9, 478. (b) Adelstein,
G. W. J. Med. Chem. 1973, 16, 309. (c) Saunders, J.; Cassidy, M.;
Freedman, S. B.; Harley, E. A.; Iversen, L. L.; Kneen, C.; MacLeod,
A. M.; Merchant, K. J.; Snow, R. J.; Baker, R. J. Med. Chem. 1990,
33, 1128. (d) Orlek, B. S.; Blaney, F. E.; Brown, F.; Clark, M. S. G.;
Hadley, M. S.; Hatcher, J.; Riley, G. J.; Rosenberg, H. E.;
Wadsworth, H. J.; Wyman, P. J. Med. Chem. 1991, 34, 2726.
(e) Fray, M. J.; Cooper, K.; Parry, M. J.; Richardson, K.; Steele, J.
J. Med. Chem. 1995, 38, 3514. (f) Omar, F. A.; Mahfouz, N. M.;
Rahman, M. A. Eur. J. Med. Chem. 1996, 31, 819. (g) Rai, L. K. M.;
Linganna, N. Farmaco 2000, 55, 389. (h) Zheng, X.; Li, Z.; Wang,
Y.; Chen, W.; Huang, Q.; Liu, C.; Song, G. J. Fluorine Chem. 2003,
123, 163. (i) Almasirad, A.; Tabatabai, S. A.; Faizi, M.;
Kebriaeezadeh, A.; Mehrabi, N.; Dalvandi, A.; Shafiee, A. Bioorg.
Med. Chem. Lett. 2004, 14, 6057. (j) Leung, D.; Du, W.; Hardouin,
C.; Cheng, H.; Hwang, I.; Cravatt, B. F.; Boger, D. L. Bioorg. Med.
Chem. Lett. 2005, 15, 1423. (k) Manojkumar, P.; Kochupappy, T.
Acta Pharm. (Zagreb, Croatia) 2009, 59, 159. (l) Srinivas, K.;
Kumar, K. P. Int. J. Biopharm. 2010, 1, 14.
(2) (a) Adachi, C.; Baldo, M. A.; Forrest, S. R.; Thompson, M. E. Appl.
Phys. Lett. 2000, 77, 904. (b) Mitschke, U.; Bäuerle, P. J. Mater.
Chem. 2000, 10, 1471. (c) Lee, Y.-Z.; Chen, X.; Chen, S.-A.; Wei,
P.-K.; Fann, W.-S. J. Am. Chem. Soc. 2001, 123, 2296. (d) Wang, J.;
Wang, R.; Yang, J.; Zheng, Z.; Carducci, M. D.; Cayou, T.;
Peyghambarian, N.; Jabbour, G. E. J. Am. Chem. Soc. 2001, 123,
6179. (e) Chan, L.-H.; Lee, R.-H.; Hsieh, C.-F.; Yeh, H.-C.; Chen,
C.-T. J. Am. Chem. Soc. 2002, 124, 6469. (f) Guan, M.; Bian, Z. Q.;
Zhou, Y. F.; Li, F. Y.; Li, Z. J.; Huang, C. H. Chem. Commun. 2003,
2708. (g) Yang, X.; Müller, D. C.; Nether, D.; Meerholz, K. Adv.
Mater. (Weinheim, Ger.) 2006, 18, 948. (h) He, G. S.; Tan, L.-S.;
Zheng, Q.; Prasad, P. N. Chem. Rev. 2008, 108, 1245.
(3) (a) Saikahi, H.; Shimojo, N.; Uehara, Y. Chem. Pharm. Bull. 1972,
20, 1663. (b) Werber, G.; Bucherri, F.; Noto, R.; Gentile, M. J. Het-
erocycl. Chem. 1977, 14, 1385. (c) Milcent, R.; Barbier, G. J. Het-
erocycl. Chem. 1983, 20, 77. (d) Jedlovská, E.; Leško, J. Synth.
Commun. 1994, 24, 1879. (e) Mruthyunjayaswamy, B. H. M.;
Shanthaveerappa, B. K. Indian J. Heterocycl. Chem. 1998, 8, 31.
(f) Flidallah, H. M.; Sharshira, E. M.; Basaif, S. A.; El-Kadar A-Ba-
Oum, A. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 67.
(g) Rostamizadeh, S.; Ghasem Housaini, S. A. Tetrahedron Lett.
2004, 45, 8753. (h) Dabiri, M.; Salehi, P.; Baghbanzadeh, M. Tet-
rahedron Lett. 2006, 47, 6983. (i) Majji, G.; Rout, S. K.; Guin, S.;
Gogoi, A.; Patel, B. K. RSC Adv. 2014, 4, 5357.
(4) (a) Yang, R.; Dai, L. J. Org. Chem. 1993, 58, 3381. (b) Dobrotă, C.;
Paraschivescu, C. C.; Dumitru, I.; Matache, M.; Baciu, I.; Ruţă, L.
L. Tetrahedron Lett. 2009, 50, 1886. (c) Rao, V. S.; Chandra
Sekhar, K. V. G. Synth. Commun. 2004, 34, 2153. (d) Shang, Z.
Synth. Commun. 2006, 36, 2927. (e) Shang, Z.; Reiner, J.; Chang,
J.; Zhao, K. Tetrahedron Lett. 2005, 46, 2701.
(7) Zarudnitskii, E. V.; Pervak, I. I.; Merkulov, A. S.; Yurochenko, A.
A.; Tolmachev, A. A. Tetrahedron 2008, 64, 10431.
(8) (a) Klingsberg, E. J. Am. Chem. Soc. 1958, 80, 5786. (b) Kerr, V. N.;
Ott, D. G.; Hayes, F. N. J. Am. Chem. Soc. 1960, 82, 186. (c) Short,
F. W.; Long, L. M. J. Heterocycl. Chem. 1969, 6, 707. (d) Reddy, C.
K.; Reddy, P. S. N.; Ratnam, C. V. Synthesis 1983, 842. (e) Al-Talib,
M.; Tashtoush, H.; Odeh, N. Synth. Commun. 1990, 20, 1811.
(9) (a) Bentiss, F.; Lagrenée, M.; Barbry, D. Synth. Commun. 2001,
31, 935. (b) Tandon, V. K.; Chhor, R. B. Synth. Commun. 2001, 31,
1727. (c) Mashraqui, S. H.; Ghadigaonkar, S. G.; Kenny, R. S.
Synth. Commun. 2003, 33, 2541. (d) Kangani, C. O.; Kelley, D. E.;
Day, B. W. Tetrahedron Lett. 2006, 47, 6497.
(10) Zhang, G.; Wen, X.; Wang, Y.; Han, X.; Luan, Z.; Ding, C.; Cao, X.
RSC Adv. 2013, 3, 22918.
(11) (a) Dong, Y.; Zhao, X.; Liu, R. Chin. J. Chem. 2015, 33, 1019.
(b) Yin, Y.; Chu, C.; Lu, Q.; Tao, J.; Liang, X.; Liu, R. Adv. Synth.
Catal. 2010, 352, 113. (c) Zhang, G.; Liu, R.; Xu, Q.; Ma, L.; Liang,
X. Adv. Synth. Catal. 2006, 348, 862.
(12) 2-tert-Butyl-5-phenyl-1,3,4-oxadiazole (2a); Typical Proce-
dure
A mixture N′-(2,2-dimethylpropylidene)benzohydrazide (1a;
0.1021 g, 0.5 mmol), Fe(NO3)3·9H2O (0.0202 g, 0.05 mmol),
MgSO4 (0.1204 g, 1.0 mmol), TEMPO (0.0078 g, 0.05 mmol), and
DCE (5.0 mL) was added to a 100 mL sealed tube and vigorously
stirred under O2 at 35 °C for 6 h. H2O (20.0 mL) was then added
to the tube and the product was extracted with CH2Cl2 (3 × 15
mL). The organic phases were combined, dried (Na2SO4), and
concentrated under a vacuum. The residue was purified by
column chromatography to give a light yellow liquid; yield:
0.0931 g (92%). 1H NMR (500 MHz, DMSO-d6): δ = 7.99 (dd, J =
8.0, 1.6 Hz, 2 H), 7.63–7.54 (m, 3 H), 1.42 (s, 9 H). 13C NMR (125
MHz, DMSO-d6): δ = 172.67, 163.77, 131.71, 129.29, 126.37,
123.58, 32.02, 27.77. HRMS: m/z [M + 1]+ calcd for C12H15N2O:
203.1179; found: 203.1178.
(13) 2,5-Diphenyl-1,3,4-oxadiazole (4a): Typical Procedure
A mixture of N′-(benzylidene)benzohydrazide (0.1120 g, 0.5
mmol), Fe(NO3)3·9H2O (0.0202 g, 0.05 mmol), MgSO4 (0.1204 g,
1.0 mmol), TEMPO (0.0078 g, 0.05 mmol), and CH2Cl2 (5.0 mL)
was added to a 100 mL sealed tube and vigorously stirred under
O2 at 35 °C for 6 h. H2O (20.0 mL) was then added to the tube
and the product was extracted with CH2Cl2 (3 × 15 mL). The
organic phases were combined, dried (Na2SO4), and concen-
trated under a vacuum. The residue was purified by column
chromatography to give a light yellow solid; yield: 0.0911 g
(82%). 1H NMR (500 MHz, DMSO-d6): δ = 8.15–8.08 (m, 4 H),
7.66–7.60 (m, 6 H). 13C NMR (125 MHz, DMSO-d6): δ = 163.99,
131.99, 129.37, 126.65, 123.33. HRMS: m/z [M + 1]+ calcd for
C
14H11N2O: 223.0871; found: 223.0867.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–E