Poormirzaei et al.
7
4. Kalyanasundaram K and Grätzel M. Coordination Chem Rev
1998; 177: 347.
5. Aihara S, Hirano Y, Tajima T, et al. Appl Phys Lett 2003; 82:
511.
6. Shi J, Chai Z, Su J, et al. Dyes Pigm 2013; 98: 405.
7. Te Velde E, Veerman T, Subramaniam V, et al. Eur J Surg
Oncology 2010; 36: 6.
8. Hsueh CL, Lu YW, Hung CC, et al. Dyes Pigm 2007; 75:
130.
9. Polo AS, Itokazu MK and Iha NYM. Coordination Chem
Rev 2004; 248: 1343.
10. Maradiya HR. J Saudi Chem Soc 2010; 14: 77.
11. Gudmundsson KS and Johns BA. Org Letters 2003; 5: 1369.
12. Wu Z, Fraley ME, Bilodeau MT, et al. Bioorg Med Chem
Lett 2004; 14: 909.
13. Geronikaki A, Babaev E, Dearden J, et al. Bioorg Med Chem
2004; 12: 6559.
14. Lima PC, Avery MA, Tekwani BL, et al. Farmaco 2002; 57:
825.
(265.3): C, 67.92; H, 4.18; N, 15.84, Found: C, 68.12; H,
4.21; N, 15.65.
1-(4-Bromophenyl)-2-(3-(hydroxyimino)imidazo[1,2-
a]pyridin-2(3H)-ylidene)ethanone (3b): Purified by a silica
gel column chromatography (CHCl3-MeOH, 18:4) to give
a dark red powder, yield (69%), mp>300°C. IR (KBr):
1569 (m) (C=C), 1631 (s) (C=O), 3374 (m) (OH) cm−1. 1H
NMR (DMSO-d6): δ=6.77 (1H, d, J=6.7Hz, pyridine H),
7.01 (1H, t, J=7.1Hz, pyridine H), 7.39 (1H, s, Alkene H),
7.55 (2H, d, J=8.6Hz, 4-bromophenyl H), 7.69–7.87 (4H,
m, ArH); 8.96 (br s, 27.5% of 1H, OH), 9.33 (br s, 23.9% of
1H, OH), 10.09 (br s, 24.2% of 1H, OH), 10.12 (br s, 24.4%
of 1H, OH). 13C NMR (DMSO-d6): δ=103.4, 113.4, 123.4,
128.3, 134.8, 135.1, 135.7, 141.6, 147.2, 152.8, 158.5,
166.8, 191.9. MS (m/z): 345 [M(81Br)]+, 343 [M(79Br)]+.
Anal. Calcd for C15H10N3O2Br (344.2): C, 52.35; H, 2.93;
N, 12.21, Found: C, 52.17; H, 2.90; N, 12.55.
3-(Hydroxyimino)imidazo[1,2-a]pyridin-2(3H)-
ylidene)-1-(4-nitrophenyl)ethanone (3c): Purified by sil-
ica gel column chromatography (CHCl3-MeOH, 4:1) to
give a dark red powder, yield (65%), mp > 300 °C. IR
(KBr): 1335, 1575 (s) (NO2), 1569 (m) (C=C), 1631 (s)
(C=O), 3374 (m) (OH) cm−1. 1H NMR (DMSO-d6):
δ = 6.81 (1H, d, J = 6.7 Hz, pyridine H), 7.02 (1H, t,
J = 7.1 Hz, pyridine H), 7.41 (1H, s, Alkene H), 7.73–7.85
(2H, m, ArH), 8.17 (2H, d, J = 8.7 Hz, 4-nitrophenyl H),
8.49 (2H, d, J = 8.7 Hz, 4-nitrophenyl H), 8.99 (br s,
28.2% of 1H, OH), 9.36 (br s, 23.0% of 1H, OH), 10.05
(br s, 23.4% of 1H, OH), 10.09 (br s, 25.4% of 1H, OH).
13C NMR (DMSO-d6): δ = 103.6, 113.9, 122.2, 124.8,
134.3, 135.1, 135.9, 147.8, 152.3, 152.8, 158.5, 166.8,
191.7. MS (m/z): 310 (M+). Anal. Calcd for C15H10N4O4
(310.3): C, 58.07; H, 3.25; N, 18.06, Found: C, 57.85; H,
3.21; N, 17.90.
15. Trapani G, Franco M, Ricciardi L, et al. J Med Chem 1997;
40: 3109.
16. Ismail MA, Brun R, Wenzler T, et al. J Med Chem 2004; 47:
3658.
17. Abe Y, Kayakiri H, Satoh S, et al. J Med Chem 1998; 41:
4053.
18. Rahimizadeh M, Pordel M, Bakavoli M, et al. Dyes Pigm
2010; 86: 266.
19. Baf MMF, Pordel M and Daghigh LR. Tetrahedron Lett
2014; 55: 6925.
20. Rahimizadeh M, Pordel M, Ranaei M, et al. J Heterocycl
Chem 2012; 49: 208.
21. Razmara S, Pordel M and Ebrahimi M. Chem Heterocyclic
Comps 2015: 51: 713.
22. Poorhaji S, Pordel M and Ramezani S. J Mol Struct 2016;
1119: 151.
23. Pordel M, Beyramabadi SA and Mohammadinejad A. Dyes
and Pigm 2014; 102: 46.
24. Roe AM. J Chem Soc 1963; 2195.
25. Paolini JP and Robins RK. J Org Chem 1965; 30: 4085.
26. Mąkosza M and Wojciechowski K. Chem Rev 2004; 104:
2631.
Declaration of conflicting interests
The author(s) declared no potential conflicts of interest with
respect to the research, authorship, and/or publication of this
article.
27. Zonozi F, Beyramabadi SA, Pordel M, et al. Res Chem
Intermed 2017; 43: 1829.
28. Tezer N and Karakus N. J Mol Model 2009; 15: 223.
29. Pordel M, Ramezani S, Jajarmi M, et al. Russ J Bioorg Chem
2016; 42: 106.
30. Pordel M, Abdollahi A and Razavi B. Russ J Bioorg Chem
2013; 39: 240.
Funding
The author(s) disclosed receipt of the following financial support
for the research, authorship, and/or publication of this article: We
express our sincere gratitude to the Research Office, Mashhad
Branch, Islamic Azad University, Mashhad, Iran, for financial
support of this work.
31. Sztaricskai F, Pintér G, Röth E, et al. J Antibiot 2007; 60:
529.
32. Joux F and Lebaron P. Microbes Infect 2000; 2: 1523.
33. Frisch M, Trucks G, Schlegel H, et al. Pittsburgh, PA, 1998.
34. Lee C, Yang W and Parr RG. Physical Rev B 1988: 37: 785.
35. Cammi R and Tomasi J. J Comput Chem 1995; 16: 1449.
36. Bauer D and Ceccherini F. Opt Express 2001; 8: 377.
37. Petersilka M, Gossmann U and Gross E. Phys Rev Lett 1996;
76: 1212.
ORCID iD
Mehdi Pordel
References
1. Bhatti HS and Seshadri S. Color technol 2004; 120: 151.
2. Shridhar AH, Keshavayya J and Hoskeri J. Int J Pharm
Pharm Sci 2002; 4: 386.
38. Bauernschmitt R and Ahlrichs R. Chem Phys Lett 1996;
256: 454.
39. Wolinski K, Hinton JF and Pulay P. J Am Chem Soc 1990;
112: 8251.
3. Faustino H, Brannigan CR, Reis LV, et al. Almeida Dyes
Pigm 2009; 83: 88.