D
A. Kędzia et al.
Letter
Synlett
(9) Patel, K. D.; Prajapati, S. M.; Panchal, S. N.; Patel, H. D. Synth.
Commun. 2014, 41, 1859.
(40) Pfister, R.; Ihalainen, J.; Hamm, P.; Kolano, C. Org. Biomol. Chem.
2008, 6, 3508.
(10) Zheng, X.; Li, Z.; Wang, Y.; Chen, W.; Huang, Q.; Liu, C.; Song, G.
J. Fluorine Chem. 2003, 123, 163.
(11) Zou, X. J.; Lai, L. H.; Zhang, Z. X. J. Agric. Food Chem. 2002, 50,
3757.
(12) Schulz, B.; Orgzall, I.; Freydank, A.; Xii, C. Adv. Colloid Interface
Sci. 2005, 116, 143.
(13) Chen, Z. K.; Meng, H.; Lai, Y. H.; Huang, W. Macromolecules
1999, 32, 4351.
(14) Tamoto, N.; Adachi, C.; Nagai, K. Chem. Mater. 1997, 9, 1077.
(15) Sinigersky, V.; Wegner, G.; Schopov, I. Eur. Polym. J. 1993, 29,
617.
(16) Homocianu, M.; Airinei, A. J. Fluoresc. 2016, 26, 1617.
(17) Kerr, N. V.; Ott, D. G.; Hayes, F. N. J. Am. Chem. Soc. 1960, 82, 186.
(18) Klinsberg, E. J. Am. Chem. Soc. 1958, 80, 5786.
(19) Tully, W. R.; Cardner, C. R.; Gillespie, R. J.; Westwood, R. J. Med.
Chem. 1991, 34, 2060.
(41) Representative Procedures
N'-[(2-Phenylhydrazinyl)carbonyl]benzohydrazide (5a)
Sodium hydrogen carbonate (2.1 g, 0.03 mol) was dissolved in
water (60 mL) and N-phenylcarbonohydrazide (3, 4 g, 0.02 mol)
was added with vigorous stirring. Then, benzoyl chloride (4a,
2.9 ml 0.03 mol) dissolved in toluene (14 mL) was added drop-
wise to the resultant slurry and the precipitate was stirred at
room temperature for 24 h. The viscous mass was cooled in an
ice bath and filtered. The product was treated with diethyl
ether, triturated, and dried. The solid was crystallized from a
mixture of ethanol and acetic acid (3:1 v/v) to give pure N'-[(2-
phenylhydrazinyl)carbonyl]benzohydrazide.
White solid (2.97 g, 55% yield). Mp 204–206 °C. IR (ATR): ν =
3325, 3219, 3057, 2162, 1683, 1632, 1601, 1576, 1521, 1485,
1442, 1418, 1333, 1315, 1304, 1257, 1217, 1175, 1152, 1090,
1074, 1026, 974, 899, 812, 750, 687 cm–1 1H NMR (400 MHz,
.
(20) Short, F. W.; Long, L. M. J. Heterocycl. Chem. 1969, 6, 707.
(21) Milcent, R.; Barbier, G. J. Heterocycl. Chem. 1983, 20, 77.
(22) Mruthyunjayaswamy, B. H. M.; Shantaveerappa, B. K. Indian J.
Heterocycl. Chem. 1998, 8, 31.
(23) Werber, G.; Bucherri, F.; Noto, R.; Gentile, M. J. Heterocycl. Chem.
1977, 14, 1385.
(24) Rostamizadeh, S.; Ghasem Housaini, S. A. Tetrahedron Lett.
2004, 45, 8753.
(25) Jedlovska, E.; Lesko, J. Synth. Commun. 1994, 24, 1879.
(26) Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Bahramnejad, M. Tetra-
hedron Lett. 2006, 47, 6983.
DMSO): δ = 6.72 (t, J = 7.2 Hz, 1 H), 6.81 (d, J = 8.0 Hz, 2 H), 7.16
(t, J = 8.2 Hz, 2 H), 7.48 (t, J = 7.6 Hz, 2 H), 7.55 (t, J = 7.2 Hz, 1 H),
7.61 (s, 1 H), 7.90 (d, J = 6.8 Hz, 2 H), 8.36 (s, 2 H), 10.13 (s, 1 H)
ppm. 13C NMR (100 MHz, DMSO): δ = 112.5, 118.6, 127.5, 128.2,
128.5, 131.5, 132.8, 149.6, 158.8, 166.1 ppm. UV-VIS: λmax
(MeOH) 275.5 nm (ε·10–3 4.76 cm–1M–1), λmax (MeOH) 231.0 nm
(ε·10–3 27.35 cm–1M–1), λmax (MeOH) 202.0 nm (ε·10–3 46.43 cm–
1M–1). Anal. Calcd for C14H14N4O2: C, 62.21; H, 5.22; N, 20.73.
Found: C, 62.22; H, 5.20; N, 20.75. HRMS calcd for (C14H14N4O2 +
H+): 271.1190; found: 271.1188.
2-Phenyl-5-phenyldiazenyl-1,3,4-oxadiazole (6a)
(27) Jasiak, K.; Kudelko, A. Tetrahedron Lett. 2015, 56, 5878.
(28) Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M. A.;
Bahramnejad, M. Synth. Commun. 2007, 37, 1201.
(29) Buscemi, S.; Cicero, M. G.; Vivona, N. J. Heterocyclic Chem. 1988,
25, 931.
(30) Buscemi, S.; Pace, A.; Vivona, N.; Caronna, T. J. Heterocyclic
Chem. 2001, 38, 777.
(31) Povazanec, F.; Kovac, J.; Svoboda, J. Collect Czech Chem. Commun.
1980, 45, 1299.
(32) Wei, R.; Xu, Z.; Liu, X.; He, Y.; Wang, X. J. Mater. Chem. C 2015, 3,
10925.
(33) Węglarz-Tomczak, E.; Górecki, Ł. CHEMIK 2012, 66, 1298.
(34) Sandin, R. B.; Cairns, T. L. Org. Synth. 1939, 29, 81.
(35) Heo, J.; Lim, C. K.; Baev, A.; Kuzmin, A. N.; Park, S. Y.; Prasad, P.
N.; Kim, S. Dyes Pigm. 2016, 130, 162.
(36) Kim, H. S.; Pham, T. T.; Yoon, K. B. J. Am. Chem. Soc. 2008, 130,
2134.
(37) Jousselme, B.; Blanchard, P.; Gallego-Planas, N.; Levillain, E.;
Delaunay, J.; Allain, M.; Richomme, P.; Roncali, J. Chem. Eur. J.
2003, 9, 5297.
N'-[(2-Phenylhydrazinyl)carbonyl]benzohydrazide (5a, 0.01 mol)
was heated with phosphorus oxychloride (19 mL) for 3 h, the
course of the reaction being monitored by TLC. The resulting
dark brown mixture was concentrated with a rotary evaporator.
Then, distilled water (100 mL) was poured into the flask, ice
cubes were added and the mixture stirred, resulting in a dark
precipitate. The mixture was left over night in a refrigerator and
then filtered. The resulting solid was purified by column chro-
matography with chloroform/ethyl acetate (5:1 v/v) as the
eluent to give pure 2-phenyl-5-phenylazenyl-1,3,4-oxadiazole.
Red solid (1.4 g, 56% yield). Mp 139–140 °C. IR (ATR): ν = 2921,
2161, 1968, 1694, 1603, 1585, 1540, 1509, 1478, 1461, 1449,
1422, 1330, 1318, 1307, 1245, 1220, 1203, 1151, 1096, 1071,
1017, 975, 959, 928, 773, 721, 702, 688, 679 cm–1. 1H NMR (400
MHz, CDCl3): δ = 7.54–7.64 (m, 6 H), 8.11 (dd, J1 =7.6 Hz, J2 = 0.8
Hz, 2 H), 8.22 (dd, J1 =8.4 Hz, J2 =1.6 Hz, 2 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 123.2, 124.4, 127.6, 128.8, 129.0, 129.2,
129.6, 132.7, 134.4, 152.8, 164.5 ppm. UV-VIS: λmax (MeOH)
348.0 nm (ε·10–3 5.97 cm–1M–1), λmax (MeOH) 261.5 nm (ε·10–3
8.33 cm–1M–1), λmax (MeOH) 202.0 nm (ε·10–3 18.16 cm–1M–1).
Anal. Calcd for C14H10N4O: C, 67.19; H, 4.03; N, 22.39. Found: C,
67.15; H, 4.01; N, 22.37. HRMS calcd for (C14H10N4O + H+):
250.0927; found: 250.0923.
(38) Luboch, E.; Wagner-Wysiecka, E.; Poleska-Muchlado, Z.;
Kravtsov, V. Tetrahedron 2005, 61, 10738.
(39) Zhao, R.; Tan, C.; Xie, Y.; Gao, C.; Liu, H.; Jiang, Y. Tetrahedron
Lett. 2011, 52, 3805.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–D