An Efficient One-Pot Synthesis of Condensed Imidazoles Using Pentafluorophenylammonium Triflate as Novel, Metal-free and Reusable Catalyst

Naser Montazeri; Abbas Esmaeili

doi:10.14233/ajchem.2013.13934

Issue

Vol. 25 No. 6 (2013): Vol 25 Issue 6

Issue Published : December 26, 2012

This work is licensed under a Creative Commons Attribution 4.0 International License.

An Efficient One-Pot Synthesis of Condensed Imidazoles Using Pentafluorophenylammonium Triflate as Novel, Metal-free and Reusable Catalyst

https://doi.org/10.14233/ajchem.2013.13934

Naser Montazeri

Department of Chemistry, Faculty of Sciences, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

Abbas Esmaeili

Department of Chemistry, Faculty of Sciences, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

Corresponding Author(s) : Naser Montazeri

montazer50@toniau.ac.ir

Asian Journal of Chemistry, Vol. 25 No. 6 (2013): Vol 25 Issue 6
Article Published : January 9, 2013

Abstract

A superior method of synthesis of condensed imidazoles by the catalytic action of pentafluorophenylammonium triflate on the reaction of 1,2-diaminoaromatics with orthoesters is described. The catalyst is reusable and can be applied several times without considerable decrease in the yields and rates of the reaction.

Keywords

Pentafluorophenylammonium triflate Reusable 1,2-Diaminoaromatic Orthoester Condensed imidazoles

Montazeri, N., & Esmaeili, A. (2013). An Efficient One-Pot Synthesis of Condensed Imidazoles Using Pentafluorophenylammonium Triflate as Novel, Metal-free and Reusable Catalyst. Asian Journal of Chemistry, 25(6), 3446–3448. https://doi.org/10.14233/ajchem.2013.13934

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References

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M.J. Yamato, J. Pharm. Soc. Jpn., 112, 81 (1992).
A. Benazzouez, T. Bround and P. Dubedat, Eur. J. Pharmacol., 284, 299 (1995).
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(a) H.O. Bourbigou, L. Magna and D. Morvan, Appl. Catal. A: Chem., 373, 1 (2010); (b) M. Ghiaci, B. Maghabarari, S. Habibollahi and A. Gil, Bioresour. Techol., 102, 1200 (2011).
(a) J.H. Chark and D.H. Macquarric, J. Chem. Soc. Rev., 303 (1996); (b) O.H. Espeel, B. Janssens and P.A. Jacobs, J. Org. Chem., 58, 7688 (1993); (c) W.F. Holderich and G. Heitmann, Catal. Today, 353 (1997).
(a) V.H. Grenda, R.E. Jones and G. Gal, J. Org. Chem., 30, 259 (1965); (b) J.P. Ferris and F.R. Antonuci, Chem. Commun., 126 (1972); (c) B. Stanvonik and M. Tisler, Synthesis, 120 (1974); (d) D. Villemin, M. Hammadi and B. Martin, Synth. Commun., 26, 2895 (1996); (e) W. Friedrich and K. Bernhour, Ber., 89, 814 (1956).
M. Israel and A.R. Day, J. Org. Chem., 24, 1455 (1959).
(a) C.E. Song, J.S. Lim and S.C. Kim, Chem. Commun., 2415 (2000); (b R.A. Sheldo and H. Van Bekku, Catalysis Through Heterogeneous Catalysis; Wiley-VCH. Weinhiem: Germany, 61 (2002).
(a) T. Okuhara, Chem. Rev., 102, 3641 (2002); (b) A. Davoodnia, Tavakoli-A. Nishabori and N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 32, 32 (2011).
M. Curini, F. Epifano and F. Montanari, Syn Lett., 1832 (2004).
K.R. Hornberger, G.M. Adjabeng and H.D. Dickson, Tetrahedron Lett., 47, 5359 (2006).
R.N. Nadaf, S.A. Siddiqui and T. Daniel, J. Mol. Catal. A, 241, 155 (2004).
B. Das, H. Hollan and Y. Srinivas, Tetrahedron Lett., 48, 61 (2007).
U. Srinivas, C.H. Srinivas and P. Navender, Catal. Commun., 8, 107 (2007).
C.D. Wilfred and R.J.K. Taylor, Synlett., 1628 (2004).
D. Saha, A. Saha and B.C. Renu, Green Chem., 11, 733 (2009).
T. Funatomi, K. Wakasugi and T. Misaki, Green Chem., 8, 1022 (2006).
A. Iida, J. Osada and R. Nagase, Org. Lett., 9, 1859 (2007).
R. Nase, J. Osada and H. Tamagaki, Adv. Synth. Catal., 352, 1128 (2010).
N. Montazeri, S. Khaksar, A. Nazari, S.S. Alavi, S.M. Vahdat and M. Tajbakhsh, J. Fluorine Chem., 132, 450 (2011).
(a) K. Pourshamsian, N. Montazeri, K. Rad-Moghadam and A. Asgari J. Heterocycl. Chem., 47, 1439 (2010); (b) F. Hatamjafari and N. Montazeri, Turk. J. Chem., 33, 797 (2009); (c) M.M. Heravi, N. Montazeri, M. Rahimizadeh, M. Bakavoli and M. Ghssemzadeh, J. Heterocycl. Chem., 42, 1021 (2005).
(a) N. Montazeri and K. Rad-Moghadam, Chin. Chem. Lett., 19, 1143 (2008); (b) N. Montazeri and K. Rad-Moghadam, Phosphorus, Sulfur and Silicon, 179, 2533 (2004); (c) N. Montazeri, Asian. J. Chem., 22, 7432 (2010); (d) N. Montazeri and K. Rad-Moghadam, Asian. J. Chem., 18, 1557 (2006); (e) M.M. Heravi, N. Montazeri, M. Rahimzadeh, M. Bakavoli and M. Ghassemzadeh, J. Chem. Res., 5, 584 (2000)

References

I. Yildiz-oren, I. Yalcin, A. Aki-sener and N. Carturk, Eur. J. Med., 39, 291 (2004).

M.J. Yamato, J. Pharm. Soc. Jpn., 112, 81 (1992).

A. Benazzouez, T. Bround and P. Dubedat, Eur. J. Pharmacol., 284, 299 (1995).

D. Kumar, M.R. Jacob and M.B. Reynolds, Bioorg. Med. Chem., 10, 3977 (2002).

D.A. Evans, C.E. Sacks and W.A. Keleschik, J. Am. Chem. Soc., 101, 6789 (1979).

(a) X. Song, B.S. Vig and P.L. Lovenzi, J. Med. Chem., 48, 1274 (2005); (b) D.J. Zhao, Amaiz and B. Griedel, Bioorg. Med. Chem. Lett., 10, 963 (2000); (c) L.B. Townsend, R.V. Devivar and S.R. Turk, J. Med. Chem., 38, 4098 (1995); (d) R. Zou, J. Drach and L.B. Townsend, J. Med. Chem., 40, 811 (1997).

(a) H.O. Bourbigou, L. Magna and D. Morvan, Appl. Catal. A: Chem., 373, 1 (2010); (b) M. Ghiaci, B. Maghabarari, S. Habibollahi and A. Gil, Bioresour. Techol., 102, 1200 (2011).

(a) J.H. Chark and D.H. Macquarric, J. Chem. Soc. Rev., 303 (1996); (b) O.H. Espeel, B. Janssens and P.A. Jacobs, J. Org. Chem., 58, 7688 (1993); (c) W.F. Holderich and G. Heitmann, Catal. Today, 353 (1997).

(a) V.H. Grenda, R.E. Jones and G. Gal, J. Org. Chem., 30, 259 (1965); (b) J.P. Ferris and F.R. Antonuci, Chem. Commun., 126 (1972); (c) B. Stanvonik and M. Tisler, Synthesis, 120 (1974); (d) D. Villemin, M. Hammadi and B. Martin, Synth. Commun., 26, 2895 (1996); (e) W. Friedrich and K. Bernhour, Ber., 89, 814 (1956).

M. Israel and A.R. Day, J. Org. Chem., 24, 1455 (1959).

(a) C.E. Song, J.S. Lim and S.C. Kim, Chem. Commun., 2415 (2000); (b R.A. Sheldo and H. Van Bekku, Catalysis Through Heterogeneous Catalysis; Wiley-VCH. Weinhiem: Germany, 61 (2002).

(a) T. Okuhara, Chem. Rev., 102, 3641 (2002); (b) A. Davoodnia, Tavakoli-A. Nishabori and N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 32, 32 (2011).

M. Curini, F. Epifano and F. Montanari, Syn Lett., 1832 (2004).

K.R. Hornberger, G.M. Adjabeng and H.D. Dickson, Tetrahedron Lett., 47, 5359 (2006).

R.N. Nadaf, S.A. Siddiqui and T. Daniel, J. Mol. Catal. A, 241, 155 (2004).

B. Das, H. Hollan and Y. Srinivas, Tetrahedron Lett., 48, 61 (2007).

U. Srinivas, C.H. Srinivas and P. Navender, Catal. Commun., 8, 107 (2007).

C.D. Wilfred and R.J.K. Taylor, Synlett., 1628 (2004).

D. Saha, A. Saha and B.C. Renu, Green Chem., 11, 733 (2009).

T. Funatomi, K. Wakasugi and T. Misaki, Green Chem., 8, 1022 (2006).

A. Iida, J. Osada and R. Nagase, Org. Lett., 9, 1859 (2007).

R. Nase, J. Osada and H. Tamagaki, Adv. Synth. Catal., 352, 1128 (2010).

N. Montazeri, S. Khaksar, A. Nazari, S.S. Alavi, S.M. Vahdat and M. Tajbakhsh, J. Fluorine Chem., 132, 450 (2011).

(a) K. Pourshamsian, N. Montazeri, K. Rad-Moghadam and A. Asgari J. Heterocycl. Chem., 47, 1439 (2010); (b) F. Hatamjafari and N. Montazeri, Turk. J. Chem., 33, 797 (2009); (c) M.M. Heravi, N. Montazeri, M. Rahimizadeh, M. Bakavoli and M. Ghssemzadeh, J. Heterocycl. Chem., 42, 1021 (2005).

(a) N. Montazeri and K. Rad-Moghadam, Chin. Chem. Lett., 19, 1143 (2008); (b) N. Montazeri and K. Rad-Moghadam, Phosphorus, Sulfur and Silicon, 179, 2533 (2004); (c) N. Montazeri, Asian. J. Chem., 22, 7432 (2010); (d) N. Montazeri and K. Rad-Moghadam, Asian. J. Chem., 18, 1557 (2006); (e) M.M. Heravi, N. Montazeri, M. Rahimzadeh, M. Bakavoli and M. Ghassemzadeh, J. Chem. Res., 5, 584 (2000)

Issue

Vol. 25 No. 6 (2013): Vol 25 Issue 6

An Efficient One-Pot Synthesis of Condensed Imidazoles Using Pentafluorophenylammonium Triflate as Novel, Metal-free and Reusable Catalyst

Corresponding Author(s) : Naser Montazeri

Abstract

Keywords

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