Indium modified AlMCM-41 catalyzed synthesis of 2,4,5-triaryl-1H imidazole derivatives

Authors

  • Santosh Shriram Katkar Department of Chemistry, MSS’s Arts, Commerce and Science College, Ambad, Dist. Jalna-431 204 Maharashtra, India.
  • Amol Haridas Kategaonkar Assistant Professor, Department of Chemistry, MVP Samaj’s G.M.D. Arts, B.W. Commerce and Science College, Sinnar, Nashik, Maharashtra 422103, India

DOI:

https://doi.org/10.48165/

Keywords:

2,4,5-Triaryl-1H-Imidazole, Mesoporous zeolite In/AlMCM-41, Heterogeneous catalyst

Abstract

We have presented a very simple, fast, general  and efficient method for synthesis of 2,4,5- triarylimidazole derivatives via condensation of  aldehydes, benzil/benzoin and ammonium  acetate in the presence of In/AlMCM-41. All the  synthesized compounds have been characterized  on the basis of elemental analysis, IR, 1H NMR,  and 13C NMR spectral studies. 

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References

Zhu J, Bienayme H. Multicomponent Reactions. Weinheim: Wiley-VCH; 2005. 2. Krasavin M, Tsirulnikov S., Nikulnikov M, Kysil V, Ivachtchenko, A. Poorly reactive 5-piperazin 1-yl-1,3,4-thiadiazol-2-amines rendered as valid substrates for Groebke–Blackburn type multi component reaction with aldehydes and isocyanides using TMSCl as a promoter. Tetrahedron Lett 2008; 49 (36): 5241-5243.

Yavari I, Sabbaghan M, Hossaini Z. Reaction between alkyl isocyanides and isopropylidene Meldrum’s acid in the presence of bidentate nucleophiles. Mol. Diversity 2007; 11(1): 1–5. 4. Shaabani A, Soleimani E, Sarvary A, Rezayan A. H. A simple and efficient approach to the synthesis of 4H-furo [3,4-b] pyrans via a three-component reaction of isocyanides. Bioorg. Med. Chem. Lett. 2008; 18(14): 3968-3970.

Banfi L, Basso A, Cerulli V, Guanti G, Riva R. Polyfunctionalized Pyrrolidines by Ugi Multicomponent Reaction Followed by Palladium-Mediated SN2‘ Cyclizations. J. Org. Chem. 2008; 73 (4), 1608–1611.

(a) Russowsky D, Lopes F A, da Silva V S S, Canto K F S, Montes D’Oca M G, Godoi M N. Multicomponent Biginelli's synthesis of 3,4-dihydropyrimidin-2(1H)-ones promoted by SnCl2.2H2O. J. Braz. Chem. Soc. 2004; 15(2), 165-169; (b) Vieira Y W, Nakamura J, Finelli F G, Brocksom U, Brocksom T J. A concise synthesis of the 1,6-disubstituted eudesmane sesquiterpene carbon skeleton. J. Braz. Chem. Soc. 2007; 18(2), 448-451.

Lee J C , Laydon J T , McDonnell P , Gallagher T F, Kumar S, Green D, McNulty D, Blumenthal N, Heys J R, Landvatter S W, Strickler J E, McLaughlin M M, Siemens I R, Fisher S M, Livi J P, White J R, Adams J L Young P R. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature 1994; 372,739–746.

Maier T, Schmierer R, Bauer K, Bieringer H,Sachse B. US. Pat. 4820335 (1989) Chem. Abstr. 1989; 111, 19494.

Lombardino J G,Wiseman E H. Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles. J. Med. Chem. 1974; 17(11), 1182-1188.

Lombardino, J. G. Gen. Offen. 1972; 155, 558. Chem. Abstr. 77 101607y.

Phillips A P, White H L , Rosen S Eur. Pat. Appl. EP. 1982; 58( ), 890. Chem. Abstr. 98, 53894z. 12. Schmierer R, Mildenberger H, Buerstell H Ger Pat. 361464 (1987). Chem Abstr. 1988; 108, 37838. 13. Heeres J, Backx L J J, Mostmans J H, Vancustem J. Antimycotic imidazoles. Part 4. Synthesis and

antifungal activity of ketoconazole, a new potent orally active broad-spectrum antifungal agent. J. Med. Chem. 1979; 22(8), 1003-1005.

Wasserscheid P, Keim W. Ionic Liquids—New “Solutions” for Transition Metal Catalysis. Angew. Chem. Int. Ed. 2000; 39(21), 3772- 3789.

Bourissou D, Guerret O, Ggabbai F T, Bertrand G. Stable Carbenes. Chem. Rev. 2000; 100 (1), 39- 92.

Satoru I. Jap. Pat. 1989; 117, 867. Chem. Abstr. 1989; 111, 214482.

Sharma S D, Hazarika P, Konwar D. An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3·3H2O. Tetrahedron Lett. 2008; 49(14), 2216- 2220.

Mohammadi A A, Mivechi M, Kefayati H. Potassium aluminum sulfate (alum): an efficient catalyst for the one-pot synthesis of trisubstituted imidazoles. Monatsh. Fur. Chem. 2008; 139(8), 935.

Sharma G, Jyothi Y, Lakshmi P. Efficient Room‐Temperature Synthesis of Tri‐ and Tetrasubstituted Imidazoles Catalyzed by ZrCl4. Synth. Commun. 2006; 36(20), 2991-3000. 20. Balalaie S, Arabanian A, Hashtroudi M S. Zeolite HY and Silica Gel as New and Efficient Heterogenous Catalysts for the Synthesis of Triarylimidazoles under Microwave Irradiation. Monatsh. Fur. Chem. 2000; 131 (9), 945–948.

Shitole NV, Shelke KF, Sonar SS , Sadaphal SA, Shingate BB, Shingare MS. L-Proline as an Efficient Catalyst for the Synthesis of 2,4,5-Triaryl-1H-Imidazoles. Bull. Korean Chem. Soc. 2009; 30(9), 1963-1966.

Khosropour AR. Synthesis of 2,4,5-trisubstituted imidazoles catalyzed by [Hmim] HSO4 as a powerful Brönsted acidic ionic liquid. Can. J. Chem. 2008; 86(3), 264-269.

Khodaei M M, Bahrami K, Kavianinia I. p-TSA Catalyzed Synthesis of 2,4,5‐Triarylimidazoles from Ammonium Heptamolybdate Tetrahydrate in TBAI. J. Chin. Chem. Soc. 2007; 54(4), 829- 833.

Parveen A, Ahemad RS, Shaikh KA, Deshmukh SP, Pawar RP. Efficient synthesis of 2,4,5-triaryl substituted imidazoles under solvent free conditions at room temperature. Arkivoc 2007; xvi, 12- 18.

Yu C, Lei M, Su W, Xie Y, Europium Triflate–Catalyzed One–Pot Synthesis Of 2,4,5– Trisubstituted–1h–Imidazoles Via A Three–Component Condensation. Synth. Commun. 2007; 37, 3301.

Mohammed AF, Kokare ND , Sangshetti JN , Shinde DB. Sulphanilic Acid Catalyzed Facile One pot Synthesis of 2,4,5-Triarylimidazoles From Benzil/Benzoin and Aromatic Aldehydes J. Korean Chem. Soc. 2007; 51(5), 418-422.

Katkar SS; Mohite PH, Gadekar LS, Vidhate KN, Lande MK. ZnO-beta zeolite: As an effective and eco-friendly heterogeneous catalyst for the synthesis of benzothiazole derivatives. Chin. Chem. Lett. 2010; 21(4), 421-425.

Katkar SS, Mohite PH, Gadekar LS, Arbad BR , Lande M K. ZnO-beta zeolite mediated simple and efficient method for the one-pot synthesis of quinoxaline derivatives at room temperature. Centr. Eur. J. Chem. 2010; 8(2), 320-325.

Katkar SS, Arbad BR, Lande MK. ZnO-Beta Zeolite Catalyzed Solvent-Free Synthesis of Polyhydroquinoline Derivatives under Microwave Irradiation. Arab J. Sci. Eng. 2011; 36( ), 39-46. 30. (a) Shinde SV, Jadhav WN, Lande MK, Gadekar LS, Arbad BR, Kondre JM., Karade NN. Scolecite as a Novel Heterogeneous Acid Catalyst for an Efficient Synthesis of 3,4- Dihydropyrimidin-2(1H)-ones Via Multi-component Biginelli Reaction. Catal. Lett. 2008; 125(1-2), 57-61; (b) Gadekar LS, Mane SR, Katkar SS, Arbad BR, Lande MK. Scolecite as an efficient heterogeneous catalyst for the synthesis of 2,4,5-triarylimidazoles. Centr. Eur. J. Chem. 2009; 7(3), 550-554.

Gadekar LS, Katkar SS, Mane SR, Arbad BR, Lande MK. Scolecite Catalyzed Facile and Efficient Synthesis of Polyhydroquinoline Derivatives through Hantzsch Multi-component Condensation. Bull. Korean. Chem. Soc. 2009; 30(11), 2532-2534.

Katkar SS, Lande MK, Arbad BR, Rathod SB. Bull. Indium Modified Mesoporous Zeolite AlMCM 41 as a Heterogeneous Catalyst for the Knoevenagel Condensation Reaction. Bull. Korean. Chem. Soc. 2010; 31(5), 1301-1304.

Published

2019-02-02

Issue

Vol. 38 No. 1 (2019): Bulletin of Pure and Applied Sciences Chemistry (Jan-Jun) 2019

Section

Articles

How to Cite

Indium modified AlMCM-41 catalyzed synthesis of 2,4,5-triaryl-1H imidazole derivatives . (2019). Bulletin of Pure and Applied Sciences-Chemistry , 38(1), 27–32. https://doi.org/10.48165/