Research Article

A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid as a Reusable Organocatalyst and Reaction Medium

Volume: 28 Number: 1 February 23, 2015
  • Rahim Hekmatshoar
  • Mojgan Kargar
  • Abdoljalil Mostashari
  • Zahra Hashemi
  • Fereshteh Goli
  • Farnoush Mousavizadeh
EN

A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid as a Reusable Organocatalyst and Reaction Medium

Abstract

2-Ethylhexanoic acid has been applied as a dual solvent-catalyst for the one-pot, four-component synthesis of 1,2,4,5-tetrasubstituted imidazoles. This naturally occurring and widely produced fatty acid exhibited remarkable catalytic activity and was easily separated by extraction. The reusability of this catalytic media was examined up to four times and no significant drop in catalytic activity was observed. Utilizing ecofriendly, low cost and commercially available reagent, short reaction times (30-90 min), very good to excellent yields (88-93) and straightforward workup procedure are the salient properties offered by this methodology.

Keywords

References

  1. [1] Horvath, I. T., Anastas, P.T., “Innovations and green chemistry”, Chem. Rev., 107: 2169-2173, (2007). [2] Dallinger, D., Kappe, C. O., “Microwave-assisted synthesis in water as solvent”, Chem. Rev., 107: 2563- 2591, (2007)
  2. [3] Constable, D. J. C., Curzons, A. D., Cunningham, V. L., “Metrics to green chemistry: Which are the best?”, Green Chem., 4: 521-527, (2002).
  3. [4] Welton, T., “Room-temperature ionic liquids. Solvents for synthesis and catalysis”, Chem. Rev., 99: 2071-2083, (1999).
  4. [5] Safaei, H. R., Shekouhy, M., Shafiee, V., Davoodi, M., “Glycerol based ionic liquid with a boron core: A new highly efficient and reusable promoting medium for the synthesis of quinazolinones”, J. Mol. Liq., 180: 139-144, (2013).
  5. [6] Lyubimov, S. E., Rastorguev, E. A., Lubentsova, K. I., Korlyukov, A. A., Davankov, V. A., “Rhodiumcontaining hypercross-linked polystyrene as a heterogeneous catalyst for the hydroformylation of olefins in supercritical carbon dioxide”, Tetrahedron Lett., 54: 1116-1119, (2013)
  6. [7] Gladysz, J. A., Curran, D. P., Horvath, I. T., “Handbook of Fluorous Chemistry”, Wiley-VCH, Weinheim, (2004).
  7. [8] Mallepalli, R., Yeramanchi, L., Bantu, R., Nagarapu, L., “Polyethylene glycol (PEG-400) as an efficient and recyclable reaction medium for the one-pot synthesis of N-substituted azepines under catalyst-free conditions”, Synlett, 2730-2732, (2011).
  8. [9] Yang, J., Li, H., Li, M., Gu, Y., “Multicomponent reactions of β-ketosulfones and formaldehyde in a biobased binary mixture solvent system composed of meglumine and gluconic acid aqueous solution”, Adv. Synth. Catal., 354: 688-700, (2012).

Details

Primary Language

English

Subjects

Engineering

Journal Section

Research Article

Authors

Mojgan Kargar This is me

Abdoljalil Mostashari This is me

Zahra Hashemi This is me

Fereshteh Goli This is me

Farnoush Mousavizadeh This is me

Publication Date

February 23, 2015

Submission Date

September 30, 2014

Acceptance Date

-

Published in Issue

Year 2015 Volume: 28 Number: 1

APA
Hekmatshoar, R., Kargar, M., Mostashari, A., Hashemi, Z., Goli, F., & Mousavizadeh, F. (2015). A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid as a Reusable Organocatalyst and Reaction Medium. Gazi University Journal of Science, 28(1), 21-26. https://izlik.org/JA43BG98CU
AMA
1.Hekmatshoar R, Kargar M, Mostashari A, Hashemi Z, Goli F, Mousavizadeh F. A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid as a Reusable Organocatalyst and Reaction Medium. Gazi University Journal of Science. 2015;28(1):21-26. https://izlik.org/JA43BG98CU
Chicago
Hekmatshoar, Rahim, Mojgan Kargar, Abdoljalil Mostashari, Zahra Hashemi, Fereshteh Goli, and Farnoush Mousavizadeh. 2015. “A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid As a Reusable Organocatalyst and Reaction Medium”. Gazi University Journal of Science 28 (1): 21-26. https://izlik.org/JA43BG98CU.
EndNote
Hekmatshoar R, Kargar M, Mostashari A, Hashemi Z, Goli F, Mousavizadeh F (February 1, 2015) A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid as a Reusable Organocatalyst and Reaction Medium. Gazi University Journal of Science 28 1 21–26.
IEEE
[1]R. Hekmatshoar, M. Kargar, A. Mostashari, Z. Hashemi, F. Goli, and F. Mousavizadeh, “A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid as a Reusable Organocatalyst and Reaction Medium”, Gazi University Journal of Science, vol. 28, no. 1, pp. 21–26, Feb. 2015, [Online]. Available: https://izlik.org/JA43BG98CU
ISNAD
Hekmatshoar, Rahim - Kargar, Mojgan - Mostashari, Abdoljalil - Hashemi, Zahra - Goli, Fereshteh - Mousavizadeh, Farnoush. “A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid As a Reusable Organocatalyst and Reaction Medium”. Gazi University Journal of Science 28/1 (February 1, 2015): 21-26. https://izlik.org/JA43BG98CU.
JAMA
1.Hekmatshoar R, Kargar M, Mostashari A, Hashemi Z, Goli F, Mousavizadeh F. A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid as a Reusable Organocatalyst and Reaction Medium. Gazi University Journal of Science. 2015;28:21–26.
MLA
Hekmatshoar, Rahim, et al. “A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid As a Reusable Organocatalyst and Reaction Medium”. Gazi University Journal of Science, vol. 28, no. 1, Feb. 2015, pp. 21-26, https://izlik.org/JA43BG98CU.
Vancouver
1.Rahim Hekmatshoar, Mojgan Kargar, Abdoljalil Mostashari, Zahra Hashemi, Fereshteh Goli, Farnoush Mousavizadeh. A Practical and Highly Efficient Synthesis of 1,2,4,5- Tetrasubstituted Imidazoles Using 2-Ethylhexanoic Acid as a Reusable Organocatalyst and Reaction Medium. Gazi University Journal of Science [Internet]. 2015 Feb. 1;28(1):21-6. Available from: https://izlik.org/JA43BG98CU