1076
R. M. Abdel-Motaleb, H. M. Bakeer, G. H. Tamam, and W. A. A. Arafa
Vol 49
REFERENCES AND NOTES
[1] Janvier, P.; Sun, X.; Bienayme, H.; Zhu, J. J Am Chem Soc
dropwisely to the residue, until the precipitation was complete.
The solid that separated out was filtered off and recrystallized
from ethanol.
2002, 124, 2560.
Pale yellow crystals in 54% yield m.p. 156ꢀC. IR (KBr,
n, cmÀ1): 3369 (NH) 1725, 1718 (C=O). MS: (m/z): 287 (M+)
(4.1%). 1H NMR (DMSO-d6) d (ppm) 1.04 (3H, t, CH2CH3),
1.60 (1H, b b, NH), 2.16 (3H, s, CH3), 3.85 (3H, s, COOCH3),
4.52 (2H, q, CH2CH3), 7.25–7.61 (5H, m, ArH). 13C NMR
(DMSO-d6, d ppm): 10.23 (CH3), 15.71 (CH2CH3), 48.82
(OCH3), 62.51 (CH2CH3), pyrrole: [116.55 (C4), 119.79 (C2),
140.13 (C5), 142.51 (C3)], Ph: [127.27, 128.72, 129.34, 131.61],
156.93 (CO2CH3), 161.22 (CO2C2H5). Anal. C16H17NO4
(287.31). Calcd.: C, 66.89%; H, 5.96%; N, 4.88%. Found: C,
67.03%; H, 5.82%; N, 5.11%.
[2] Palmer, D. C. In Oxazoles Synthesis, Reactions and
Spectroscopy; Ed.; John Wiley & Sons, Hoboken, N. J., 2004; Vol. 60
Part B, pp 1.
[3] Jin, Z. Nat Prod Rep 2009, 26, 382.
[4] Nisha, S.; Sudhir, K. B.; Ashok, K. Eur J Med Chem 2008,
43, 2597.
[5] Malek, T. M.; Ghasem, M.; Nourollah, H.; Ali, A.; Roya, K.
Tetrahedron Lett 2007, 48, 3197.
[6] Xin-Hua, L.; Jing, Z.; An-na, Z.; Bao-An, S.; Hai-Liang, Z.;
Shan, B.; Pinaki, S. B.; Chun-Xiu, P. Bioorg Med Chem 2009, 17, 1207.
[7] Akio, S.; Asami, M.; Yuji, H. Tetrahedron Lett 2010, 51, 2247.
[8] Jianmin, Z.; Marco, A. C. Tetrahedron Lett 2010, 51, 4699.
[9] Yosuke, H.; Yuki, F.; Naohiro, S.; Shin-ichi, I.; Kazunori, O.
Tetrahedron Lett 2008, 49, 2005.
[10] Kazuaki, S.; Masahito, Y.; Takayuki, D.; Takashi, T.;
Tetrahedron Lett 2010, 51, 1674.
[11] Rao, Y. S.; Filler, R. Synthesis 1975, 12, 749.
[12] Monk, K. A.; Sarapa, D.; Mohan, R. S. Synth Commun 2000,
30, 3167.
Synthesis of 12a,b. The oxazolone 2m (0.01 mol) in dioxane
(30 mL) was boiled with aniline or p-toludine (0.01 mol) for
5 h. The mixture was cooled and poured into water (100 mL).
The solid was filtered off and recrystallized from a proper solvent.
Ethyl 3-(5-oxo-1,2-diphenyl-1H-imidazol-4(5H)-ylidene)
butanoate 12a. Recrystallized from dioxane to give yellow
crystals in 50% yield m.p. 205ꢀC. IR (KBr, n, cmÀ1): 1715, 1673
[13] Blasco, J.; Cativiels, C.; Diaz de Villegas, M. D.; Garcia, J. I.;
Jaime C.; Mayoral, J. A. Heterocycles 1988, 27, 2567.
[14] Glaser, R.; Twaik, M. Tetrahydron Lett 1979, 8, 737.
[15] Rao, Y. S. J. Org Chem 1976, 41, 722.
1
(C=O). MS: (m/z, %): 348 (M+) (28.2%). H NMR (DMSO-d6)
d (ppm): 1.27 (3H, t, CH2CH3), 1.72 (3H, s, CH3), 3.04 (2H, s,
CH2), 4.23 (2H, q, CH2CH3), 7.32–7.43 (5H, m, ArH), 7.63–7.66
(5H, m, ArH). Anal. C21H20N2O3 (348.40), Calcd.: C, 72.40%; H,
5.79%; N, 8.04%, Found: C, 72.30%; H, 5.52%; N, 7.87%.
Ethyl 3-(5-oxo-2-phenyl-1-(p-tolyl)-1H-imidazol-4(5H)-ylidene)-
butanoate 12b. Recrystallized from DMF to give yellow crystals in
47% yield m.p. 247ꢀC. IR (KBr, n, cmÀ1): 1723, 1679 (C=O). MS:
(m/z, %): 362 (M+) (34.66%). Anal. C22H22N2O3 (362.42), Calcd.:
C, 72.91%; H, 6.12%; N, 7.73%, Found: C, 72.88%; H, 6.00%;
N, 7.47%.
Synthesis of ethyl 3-(6-oxo-3-phenyl-1,6-dihydro-1,2,4-
triazin-5(2H)-ylidene)butanoate 14a. The oxazolone 2m
(0.01 mol) was suspended in ethanol (50 mL) and treated with
hydrazine hydrate (0.01 mol) at room temperature. The mixture
was stirred over night at room temperature. The solid product
that separated was filtered off and recrystallized from ethanol to
give yellow crystals in 50% yield m.p. 230ꢀC. IR (KBr,
n, cmÀ1): 1725, 1663 (C=O). MS: (m/z, %): 287 (M+) (4.1).
Anal. C15H17N3O3 (287.31), Calcd.: C, 62.71%; H, 5.96%; N,
14.63%, Found: C, 62.98%; H, 5.75%; N, 14.69%.
Synthesis of ethyl 3-(6-oxo-2,3-diphenyl-1,6-dihydro-1,
2,4-triazin-5(2H)-ylidene)butanoate 14b. A solution of 2m
(0.01 mol) in ethanol (30 mL) was treated with phenyl hydrazine
(0.01 mol), and the reaction mixture was refluxed for 5 h. The
solid product obtained after concentration of the solution was
collected by filtration and recrystallized from dioxane to give
yellow crystals in 58% yield m.p. 277ꢀC. IR (KBr, n, cmÀ1):
3213 (NH), 1719, 1666 (C=O). MS: (m/z, %): 363 (M+) (2.8%).
1H NMR (DMSO-d6) d (ppm): 1.12 (3H, t, CH2CH3), 1.70 (3H,
s, CH3), 2.65 (2H, s, CH2), 4.20 (2H, q, CH2CH3), 7.53–7.63
(5H, m, PhN), 7.99–8.03 (5H, m, PhC), 9.42 (1H, s, NH). Anal.
C21H21N3O3 (363.41), Calcd.: C, 69.41%; H, 5.82%; N, 11.56%,
Found: C, 69.22%; H, 5.75%; N, 11.71%.
[16] Cativiels S.; Melendez, E. Synthesis 1979, 10, 832.
[17] Plöchl, J. Ber 1883, 16, 2815.
[18] Erlenmeyer, E. Ann 1892, 271, 137.
[19] Shantham, R. P.; Venkatratnam, R. V. Indian J Chem 1994,
33B, 984.
[20] Dakin, H. D. J Biol Chem 1911, 9, 151.
[21] Kidwai, M.; Kumar, R. Org Prep Proceds Int 1998, 34, 451.
[22] Kumar, R.; Mishra, H. D.; Mukerjee, A. K. Synthesis 1980,
10, 836.
[23] Cativiels, C. D.; Villegas, J. A.; Mayoral, E. M. Synthesis
1983, 11, 899.
[24] Ramage, G. R.; Simonsen, J. L. J Chem Soc 1935, 57, 532.
[25] William, A.; Mohammed, J. Iraq Chem Soc 1976, 1, 63.
[26] Michael, B. W.; Mark, E. A.; Toufike, K.; Clifford, D. M.;
Douglas, R. D.; Victoria, A. F.; Shawn, M. O.; Lihong, S.; Petro, H.; Qing
D. Bioorg Med Chem Lett 2010, 20, 4156.
[27] Mariangela, B.; Giulio, C. P.; Giovanna, P.; Alessandro, De L.;
Rita, M.; Edda, De R.; Fabrizio, M.; Maurizio, B. Eur J Med Chem 2009,
44, 4734.
[28] Harrak, Y.; Rosell, G.; Daidone, G.; Plescia, S.; Schillaci, D.;
Pujol, M. D. Bioorg Med Chem 2007, 15, 4876.
[29] Black, D. In Hetarenes and Related Ring Systems: Science of
Synthesis; Maas, G., Ed.; George Thieme: Stuttgart, 2000; Vol. 9, Chapter
9.13, pp 441.
[30] Bergman, J.; Janosik, T. In Comprehensive Heterocyclic
Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor,
R. J. K., Eds.; Elsevier: Oxford, 2008; pp 269.
[31] Alias, M.; Lopez, M. P.; Cativiels, C. Tetrahedron 2004, 60, 885.
[32] Ho, J. Z.; Hohareb, R. M.; Ahn, J. H.; Sim, T. B.; Rapoport, H.
J Org Chem 2003, 68, 109.
[33] Lingaiah, N.; Satyender, A.; Rajashaker, B.; Srinivas, K.; Ruparani,
P.; Radhika, K.; Subhashini, G. Bioorg Med Chem Lett 2008, 18, 1167.
[34] Yun-Nan, Y.; Wen-long, P.; Hua-Can, S. Dyes Pigments
2010, 86, 249.
[35] Saettone, M. F. J Org Chem 1966, 31, 1959.
[36] Krieg, B.; Lautenschlager, H. L. Ann Chem 1976, 9, 208.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet