Poly(N-‎vinylimidazole): A ‎biocompatible‎, efficient, and ‎highly ‎‎recyclable ‎heterogeneous ‎catalyst for ‎the ‎preparation of ‎bis(3-‎‎indolyl)methanes ‎

Authors

  • Hayedeh Gorjian Department of Food Science ‎and Technology, Sari ‎Agricultural Sciences and ‎Natural ‎Resources ‎University, Sari, Iran
  • Hoda Fahim Department of Food Science ‎and Technology, Sari ‎Agricultural Sciences and ‎Natural ‎Resources ‎University, Sari, Iran
  • Dr. Nader Ghaffari Khaligh

Abstract

Poly(N-vinylimidazole) (PVIm), as a biocompatible, efficient, halogen-free, and reusable catalyst, was ‎applied for the solvent-free synthesis of a library of bis(3-indolyl)methanes. The reaction was ‎smoothly carried out under mild conditions, and the crude products were purified easily, and ‎the pure products were obtained in high to excellent yields.‎

Downloads

Download data is not yet available.

References

‎1. A. El-Gamal, W. L. Wang, C. Y. Duh, Sulfur-containing polybromoindoles from the formosan red alga Laurencia brongniartii. J. Nat. Prod. 2005, 68, 815-817.

T. Endo, M. Tsuda, J. Fromont, J. Kobayashi, A. Hyrtinadine, a bis-indole alkaloid from a marine sponge. J. Nat. Prod. 2007, 70, 423-424.

T. R. Garbe, M. Kobayashi, N. Shimizu, N. Takesue, M. Ozawa, H. Yukawa, Indolyl carboxylic acids by condensation of indoles with alpha-keto acids. J. Nat. Prod. 2000, 63, 596-598.

N. Sirisoma, A. Pervin, J. Drewe, B. Tseng, S. X. Cai, Discovery of substituted N'-(2-oxoindolin-3-ylidene)benzohydrazides as new apoptosis inducers using a cell- and caspase-based HTS assay. Bioorg. Med. Chem. Lett. 2009, 9, 2710-2713.

G. W. Gribble, In Comprehensive Heterocyclic Chemistry, vol. 2, second ed., Pergamom Press, New York, 1996, pp. 211.

B. P. Bandgar, K. A. Shaikh, Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions. Tetrahedron Lett. 2003, 44, 1959-1961.

J. M. Frost, M. J. Dart, K. R. Tietje, T. R. Garrison, G. K. Grayson, A. V. Daza, O. F. E-Kouhen, L. N. Miller, L. Li, B. B. Yao, G. C. Hsieh, M. Pai, C. Z. Zhu, Antinociceptive (aminoalkyl)indoles. J. Med. Chem. 2008, 51, 1904-1912.

M. C. Pirrung, Z. Li, E. Hensley, Y. Liu, A. Tanksale, B. Lin, A. Pai, N. J. G. Webster, Parallel synthesis of indolylquinones and their cell-based insulin mimicry. J. Comb. Chem. 2007, 9, 844-854.

M. A. Zeligs, Diet and estrogen status: The cruciferous connection. J. Med. Food 1998, 1, 67-82.

B. Pal, V. S. Giri, P. Jaisankar, First indium trichloride catalyzed self-addition of indoles: One pot synthesis of indolylindolines. Catal. Commun. 2005, 6, 711-715. doi: 10.1016/j.catcom.2005.07.003

B. P. Bandgar, A. V. Patil, V. T. Kamble, Fluoroboric acid adsorbed on silica gel catalyzed synthesis of bisindolyl alkanes under mild and solvent-free conditions. Arkivoc 2007, 16, 252-259.

M. L. Deb, P. J. Bhuyan, Uncatalyzed Michael addition of indoles: synthesis of some novel 3-alkylated indoles via a three-component reaction in solvent-free conditions. Tetrahedron Lett. 2007, 48, 2159-2163.

A. Hasaninejad, A. Zare, H. Sharghi, K. Niknam, M. Shekouhy, P2O5/SiO2 as an efficient, mild, and heterogeneous catalytic system for the condensation of indoles with carbonyl compounds under solvent-free conditions. Arkivoc 2007, 14, 39-50.

J. T. Li, H. G. Dai, W. Z. Xu, T. S. Li, An efficient and practical synthesis of bis(indolyl)methanes catalyzed by aminosulfonic acid under ultrasound. Ultrason. Sonochem. 2006, 13, 24-27.

J. S. Yadav, B. V. S. Reddy, B. Padmavani, M. K. Gupta, Gallium(III) halide-catalyzed coupling of indoles with phenylacetylene: synthesis of bis(indolyl)phenylethanes. Tetrahedron Lett. 2004, 45, 7577-7579.

M. Karthik, C. J. Magesh, P. T. Perumal, M. Palanichamy, B. Arabindoo, V. Murugesan, Zeolite-catalyzed ecofriendly synthesis of vibrindole A and bis(indolyl)methanes. Appl. Catal. A Gen. 2005, 286, 137-141.

C. J. Magesh, R. Nagarajan, M. Karthik, P. T. Perumal, Synthesis and characterization of bis(indolyl)methanes, tris(indolyl)methanes and new diindolylcarbazolylmethanes mediated by Zeokarb-225, a novel, recyclable, eco-benign heterogenous catalyst. Appl. Catal. A Gen. 2004, 266, 1-10.

S. Palaniappan, A. John, Facile synthesis of bis(indolyl)methanes using polyindole salt as reusable catalyst. J. Mol. Catal. A Chem. 2005, 242, 168-172.

S. J. Ji, S. Y. Wang, Y. Zhang, T. P. Loh, Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions. Tetrahedron 2004, 60, 2051-2055.

M. Chakraborty, N. Ghosh, R. Basak, Y. Harigaya, Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: a mild, expedient synthesis of diindolylalkanes and vibrindole A. Tetrahedron Lett. 2002, 43, 4075-4078.

X. F. Zeng, S. J. Ji, S. Y. Wang, Novel method for synthesis of unsymmetrical bis(indolyl)alkanes catalyzed by ceric ammonium nitrate (CAN) under ultrasonic irradiation. Tetrahedron 2005, 61, 10235-10241.

S. Ko, C. Lin, Z. Tu, Y. F. Wang, C. C. Wang, C. F. Yao, CAN and iodine-catalyzed reaction of indole or 1-methylindole with α,β-unsaturated ketone or aldehyde. Tetrahedron Lett. 2006, 47, 487-492.

S. Kobayashi, M. Araki, M. Yasuda, One-pot synthesis of β-amino esters from aldehydes using lanthanide triflate as a catalyst. Tetrahedron Lett. 1995, 36, 5773-5776.

L. Wang, J. H. Han, T. Sheng, J. Z. Fan, X. Tang, Rare earth perfluorooctanoate [RE(PFO)3]-catalyzed condensations of indole with carbonyl Compounds. Synlett 2005, 337-339.

X. Li, J. Y. Wang, W. Yu, L. M. Wu, PtCl2-catalyzed reactions of o-alkynylanilines with ethyl propiolate and dimethyl acetylenedicarboxylate. Tetrahedron 2009, 65, 1140-1146.

X. Mi, S. Luo, J. He, J. P. Cheng, Dy(OTf)3 in ionic liquid: an efficient catalytic system for reactions of indole with aldehydes/ketones or imines. Tetrahedron Lett. 2004, 45, 4567-4570.

S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, S. J. Taylor, Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation. J. Chem. Soc. Perkin Trans. 1 2000, 3815-4195.

M. G. Chung, H. W. Kim, B. R. Kim, Y. B. Kim, Y. H. Rhee, Biocompatibility and antimicrobial activity of poly(3-hydroxyoctanoate) grafted with vinyl imidazole. Int. J. Biol. Macromol. 2012, 50, 310-316.

I. C. Alupei, M. Popa, A. Bejenariu, S. Vasiliu, V. Alupei, Composite membranes based on gellan and poly(N-vinylimidazole). Synthesis and characterization. Eur. Polym. J. 2006, 42, 908-916.

C. Fodor, J. Bozi, M. Blazsó, B. Iván, Thermal behavior, stability, and decomposition mechanism of poly(N-vinylimidazole). Macromolecules 2012, 45, 8953-8960.

E. E. B. Anderson, T.E. Long, Imidazole- and imidazolium-containing polymers for biology and material science applications. Polymer 2010, 51, 2447-2454.

A. Horta, M. J. S. Molina, M. R. Gómez-Antón, I. S. F. Piérola, The pH inside a pH-sensitive gel swollen in aqueous salt solutions: poly(N-vinylimidazole). Macromolecules 2009, 42, 1285-1292.

N. Pekel, O. Güven, Separation of heavy metal ions by complexation on poly(N-vinylimidazole) hydrogels. Polym. Bull. 2004, 51, 307-314.

H. Bessbousse, T. Rhlalou, J. F. Verchère, L. Lebrun, Mercury removal from waste water using a poly(vinylalcohol)/poly(vinylimidazole) complexing membrane. Chem. Eng. J. 2010, 164, 37-48.

N. G. Khaligh, N.G. Poly(N-vinylimidazole) as an efficient catalyst for acetylation of alcohols, phenols, thiols and amines under solvent-free conditions. RSC Adv. 2013, 3, 99-110.

N. G. Khaligh, T. Mihankhah, Aldol condensations of a variety of different aldehydes and ketones under ultrasonic irradiation using poly(N-vinylimidazole) as a new heterogeneous base catalyst under solvent-free conditions in a liquid-solid system. Chin. J. Catal. 2013, 34, 2167-2173.

N. G. Khaligh, Poly(N-vinylimidazole) as a halogen-free and efficient catalyst for N-Boc protection of amines under solvent-free conditions. RSC Adv. 2012, 2, 12364-12370.

I. P. Beletskaya, E. A. Tarasenko, A. R. Khokhlov, V. S. Tyurin, Poly(N-vinylimidazole) as an efficient and recyclable catalyst of the aza-Michael reaction in water. Russ. J. Org. Chem. 2010, 46, 461-467.

Z. Chen, J. Yang, D. Yin, Y. Li, S. Wu, J. Lu, J. Wang, Fabrication of poly(1-vinylimidazole)/mordenite grafting membrane with high pervaporation performance for the dehydration of acetic acid. J. Membr. Sci. 2010, 349, 175-182.

A. H. Tian, J. -Y. Kim, J. Y. Shi, K. Kim, Poly(1-vinylimidazole)/Pd-impregnated Nafion for direct methanol fuel cell applications. J. Power Sources 2008, 183, 1-7.

K. Yao, Z. Wang, J. Wang, S. Wang, Biomimetic material-poly(N-vinylimidazole)-zinc complex for CO2 separation. Chem. Commun. 2012, 48, 1766-1768.

L. Cheng, P. –B. Zhang,Y. –F. Zhao, L. –P. Zhu, B. –K. Zhu,Y. -Y. Xu, Preparation and characterization of poly(N-vinylimidazole) gel-filled nanofiltration membranes. J. Membrane Sci. 2015, 492, 380-391.

F. Shirini, N. G. Khaligh, Succinimide‐N‐sulfonic acid catalyzed synthesis of bis(indolyl)methane and coumarin derivatives under mild conditions. Chin. J. Catal. 2013, 34,1890-1896.

C. Ramesh, N. Ravindranath, B. Das, Electrophilic substitution reactions of indoles with carbonyl compounds using ceric ammonium nitrate: A novel and efficient method for the synthesis of di- and tri-indolylmethanes. J. Chem. Res. (S) 2003, 72-74.

M. Xia, S. Wang, W. Yuan, Lewis acid catalyzed electrophilic substitution of indole with aldehydes and Schiff's bases under microwave solvent‐free irradiation. Synth. Commun. 2004, 34, 3175-3182.

A. Kamal, A. A. Qureshi, Syntheses of some substituted di-indolylmethanes in aqueous medium at room temperature. Tetrahedron 1963, 19, 513-520.

G. Babu, N. Sridhar, P. T. Perumal, A Convenient Method of Synthesis of Bis-Indolylmethanes: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases. Synth. Commun. 2000, 30, 1609-1614.

D. G. Gu, S. J. Ji, Z. Q. Jiang, M. F. Zhou, T. P. Loh, An efficient synthesis of bis(indolyl)methanes catalyzed by recycled acidic ionic liquid. Synlett 2005, 959-962.

J. Azizian, F. Teimouri, M. R. Mohammadizadeh, Ammonium chloride catalyzed one-pot synthesis of diindolylmethanes under solvent-free conditions. Catal. Commun. 2007, 8, 1117-1121.

G. V. M. Sharma, J. J. Reddy, P. S. Lakshmi, P. R. Krishna, A versatile and practical synthesis of bis(indolyl)methanes/bis(indolyl)glycoconjugates catalyzed by trichloro-1,3,5-triazine. Tetrahedron Lett. 2004, 45, 7729-7732.

J. Brandrup, E. H. Immergut, E. Grulke, Solution Properties, in Polymer Handbook, Wiley, New York, 4th edn, 1999.

Downloads

Published

2021-10-07

How to Cite

Gorjian, H., Fahim, H., & Khaligh, D. N. G. (2021). Poly(N-‎vinylimidazole): A ‎biocompatible‎, efficient, and ‎highly ‎‎recyclable ‎heterogeneous ‎catalyst for ‎the ‎preparation of ‎bis(3-‎‎indolyl)methanes ‎. Malaysian Catalysis-An International Journal, 1(1), 15–25. Retrieved from https://jml.um.edu.my/index.php/MCIJ/article/view/31301

Issue

Section

Articles