M. A. Nasseri et al.
Table 2. Comparison of results using NiO nanoparticles with those ob-
tained by other studies for the synthesis of quinolines
kind of light green sediment was formed. After the reaction was
completed, the precipitated powders were filtered and washed
with deionized water to neutral to remove the adsorbed ions and
chemicals so as to reduce the potential for agglomeration. After
being dried in an oven at 90 °C for 6 h, the precursor was calcined
in a muffle furnace at 400 °C for 1 h to afford the products with a
dark colour (NiO nanoparticles).
Entry
Catalyst
Condition
Yield (%)a Ref.
1
2
3
4
5
6
7
8
9
Current
Ethylene glycol, 100 °C, 2 h
CH3CN, 60 °C, 3 h
EtOH, reflux, 8 h
85
92
88
90
87
60
62
80
90
68
—
[35]
HClO4–SiO2
PMA–SiO2
Zr(DS)4
[36]
[37]
[38]
[39]
[39]
[40]
[39]
[41]
H2O, reflux, 6 h
Zr(HSO4)4
H2O, reflux, 13 h
General procedure for preparation of quinoline derivatives
CH3COOH (1 eq.) H2O, 60 °C, 6 h
p-TsOH (1 eq.)
bmimCl–ZnCl2
H3PO4 (1 eq.)
H2O, 60 °C, 6 h
To a mixture of carbonyl compounds (1.0 mmol), 2-amino-5-
chlorobenzophenone or 2-aminobenzophenone (1.0 mmol) and
ethylene glycol (0.1 ml) was added nano-NiO (0.004 g). The mixture
was stirred at 100 °C for the appropriate reaction time (Table 1).
The progress of the reaction was monitored by TLC. After comple-
tion of the reaction, the mixture was dissolved in acetone and the
catalyst was isolated by centrifugation. Then the solvent was re-
moved from solution under reduced pressure and the resulting
product was purified by recrystallization using ethanol to afford
the pure quinoline product in excellent purity and yield. Structural
assignments of the products are based on their 1H NMR, 13C NMR,
mass and IR spectra.
Ionic liquid, r.t., 24 h
H2O, 60 °C, 12 h
10 HCl
H2O, 100–200 °C, 1 h
Acknowledgement
We gratefully acknowledge the support of this work by the Birjand
University Research Council.
Figure 14. Recycling of catalyst for the synthesis of quinolines.
References
[1] K. M. Dooley, S. Y. Chen, J. R. Ross, J. Catal. 1994, 145, 402.
[2] H. X. Yang, Q. F. Dong, X. H. Hu, J. Power Sources 1999, 79, 256.
[3] I. Hotový, J. Huran, L. Spiess, R. Čapkovic, Š. Haščı, Vacuum 2000, 58, 300.
[4] E. L. Miller, R. E. Rocheleau, J. Electrochem. Soc. 1997, 144, 3072.
[5] G. Wang, X. Lu, T. Zhai, Y. Ling, H. Wang, Y. Tong, Y. Li, Nanoscale 2012,
4, 3123.
[6] Y. Ichiyanagi, N. Wakabayashi, J. Yamazaki, S. Yamada, Y. Kimishima,
E. Komatsu, H. Tajima, Physica B 2003, 329–333, 862.
[7] S. A. Makhlouf, F. T. Parker, F. E. Spada, A. E. Berkowitz, J. Appl. Phys.
1997, 84, 5561.
[8] X. Y. Deng, Z. Chen, Mater. Lett. 2004, 58, 276.
[9] V. Biju, M. Abdul Khadar, Mater. Sci. Eng. A 2001, 304, 814.
[10] Y. Wang, J. Zhu, X. Yang, L. Lu, X. Wang, Thermochim. Acta 2005, 437,
106.
Scheme 3. Proposed mechanism for the synthesis of quinoline in the
presence of nano-NiO.
[11] M. P. Maguire, K. R. Sheets, K. McVety, A. P. Spada, A. J. Zilberstein, Med.
Chem. 1994, 37, 2129.
[12] R. D. Larsen, E. G. Corley, A. O. King, J. D. Carrol, P. Davis, T. R. Verhoeven,
P. J. Reider, M. Labelle, J. Y. Gauthier, Y. B. Xiang, R. J. Zamboni, J. Org.
Chem. 1996, 61, 3398.
[13] Y. L. Chen, K. C. Fang, J. Y. Sheu, S. L. Hsu, C. C. Tzeng, J. Med. Chem.
2001, 44, 2374.
Plant collection and extraction
Tamarix serotina flowers were collected in July 2014 from South
Khorasan province, Iran. The AP and R of these plants were sepa-
rated, washed, shade-dried in air and ground in a mixer. Plant pow-
der (10 g) was added to 100 ml of water and the mixture was stirred
for 5 min at boiling temperature and filtered to obtain a clear
extract.
[14] G. Roma, M. D. Braccio, G. Grossi, F. Mattioli, M. Ghia, Eur. J. Med. Chem.
2000, 35, 1021.
[15] B. Kalluraya, S. F. Sreenivasa, Farmaco 1998, 53, 399.
[16] D. Doube, M. Blouin, C. Brideau, C. Chan, S. Desmarais, D. Eithier,
J. P. Fagueyret, R. W. Friesen, M. Girard, Y. Girard, J. Guay, P. Tagari,
R. N. Young, J. Bioorg. Med. Chem. Lett. 1998, 8, 1255.
[17] T. C. Ko, M. J. Hour, J. C. Lien, C. M. Teng, K. H. Lee, S. C. Kuo, L. Huang,
J. Bioorg. Med. Chem. Lett. 2001, 11, 279.
Synthesis of NiO nanoparticles
[18] Z. H. Skraup, Monatsh. Chem. 1880, 1, 316.
[19] N. D. Heindel, T. A. Brodof, J. E. Kogelschatz, J. Heterocycl. Chem. 1966,
3, 222.
[20] I. Hermecz, G. Kereszturi, L. Vasvari-Debreczy, Adv. Heterocycl. Chem.
1992, 54, 1.
[21] W. Pfitzinger, J. Prakt. Chem. 1886, 33, 100.
[22] P. K. Calaway, H. R. Henze, J. Am. Chem. Soc. 1939, 61, 1355.
[23] P. Friedländer, Chem. Ber. 1882, 15, 2572.
Nickel nitrate hexahydrate (2.63 g) was accurately weighed and dis-
solved into 40 ml of deionized water and placed under ultrasonic
treatment. Ni(NO3)2Á6H2O solution (30 ml) was mixed with 30 ml
of the obtained biological extract and the two solutions were mixed
in a beaker and stirred with a magnetic stirrer at room temperature
until a homogeneous solution was obtained. Thereafter, the mix-
ture was transferred into a round-bottom flask, sealed and main-
tained heating at 115 °C for 1.5 h in an oil bath. In this process, a
[24] E. A. Fehnel, J. Org. Chem. 1966, 31, 2899.
[25] R. Long, K. Schofield, J. Chem. Soc. 1953, 3161.
wileyonlinelibrary.com/journal/aoc
Copyright © 2016 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. (2016)