Poly(4-vinylpyridine)iodonium triiodide: A new efficient catalyst for the synthesis of 3,3-diheteroaromatic oxindole analogues

Authors

  • SUZAIMI JOHARI Nanotechnology and Catalysis Research Center, Universiti Malaya
  • NADER GHAFFARI KHALIGH Nanotechnology Catalysis and Research Centre, Universiti Malaya

Keywords:

Iodine, Poly(4-vinylpyridine), Functionalized polymer, 3,3-Diheteroaromatic oxindole

Abstract

The synthesis of a series of 3,3-diheteroaromatic oxindoles has been effectively produced through treatment of indole-2,3-dione (isatin) with various indoles and pyrroles using quaternized poly(4-vinylpyridine)iodinium iodide , under solvent-free condition and neutral medium. The reaction proceeds rapidly with excellent yields. This catalyst has been shown to be stable and highly recyclable.

Downloads

Download data is not yet available.

Author Biography

NADER GHAFFARI KHALIGH, Nanotechnology Catalysis and Research Centre, Universiti Malaya

Dr. Nader Ghaffari Khaligh received his Ph.D. in Organic chemistry from the University of Guilan, Iran, in 2013. Since 2015 he works as a researcher in the Nanotechnology & Catalysis Research Center, Universiti Malaya, Malaysia. His publications, including papers, reviews, and mini-reviews, are focused on heterogeneous and homogeneous catalysis, sustainable chemistry and energy, synthesis of heterocycles, and multi-task reagents such as Ionic liquids and Functional polymers. ‎ He has been elected as World's Top 2% Scientist Career-Long Citation ‎Impact and World's Top 2% Scientists by Stanford University in 2019, 2020, 2021, and 2022. He is the Associate Editor and Section Editor of two international journals and an Editorial board member of a few international journals.

References

Akelah A, Sherrington DC. Application of functionalized polymers in organic synthesis. Chem Rev 1981;81:557–87.

Akelah A, Sherrington DC. Recent developments in the application of functionalized polymers in organic synthesis. Polymer (Guildf) 1983;24:1369–86.

Vidal F, Jäkle F. Functional Polymeric Materials Based on Main-Group Elements. Angew Chemie - Int Ed 2019;58:5846–70.

Rosenfeld L. Discovery and Early Uses of Iodine. J Chem Educ 2000;77:984.

Ishihara K. Concepts in Iodine Catalysis. Iodine Catal. Org. Synth., Wiley; 2022, p. 11–26.

Singh F V., Shetgaonkar SE, Krishnan M, Wirth T. Progress in organocatalysis with hypervalent iodine catalysts. Chem Soc Rev 2022;51:8102–39.

Togo H, Iida S. Synthetic Use of Molecular Iodine for Organic Synthesis. Synlett 2006;2006:2159–75.

Banerjee AK, Vera W, Mora H, Laya MS, Bedoya L, Cabrera E V. Iodine in Organic Synthesis. ChemInform 2006;37:299–308.

Wang X, Yan F, Wang Q. Molecular iodine: Catalysis in heterocyclic synthesis. Synth Commun 2021;51:1763–81.

Khetmalis YM, Shivani M, Murugesan S, Chandra Sekhar KVG. Oxindole and its derivatives: A review on recent progress in biological activities. Biomed Pharmacother 2021;141:111842.

Sharma S, Monga Y, Gupta A, Singh S. 2-Oxindole and related heterocycles: synthetic methodologies for their natural products and related derivatives. RSC Adv 2023;13:14249–67.

Saraswat P, Jeyabalan G, Hassan MZ, Rahman MU, Nyola NK. Review of synthesis and various biological activities of spiro heterocyclic compounds comprising oxindole and pyrrolidine moities. Synth Commun 2016;46:1643–64.

Sakla AP, Kansal P, Shankaraiah N. Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review. European J Org Chem 2021;2021:757–72.

Kaur M, Singh M, Chadha N, Silakari O. Oxindole: A chemical prism carrying plethora of therapeutic benefits. Eur J Med Chem 2016;123:858–94.

Boddy AJ, Bull JA. Stereoselective synthesis and applications of spirocyclic oxindoles. Org Chem Front 2021;8:1026–84.

Grzyb B, Machnikowski J, Weber JV. Mechanism of co-pyrolysis of coal-tar pitch with polyvinylpyridine. J Anal Appl Pyrolysis 2004;72:121–30.

Khalig NG. Investigation of the catalytic activity of poly(4-vinylpyridine) supported iodine as a new, efficient and recoverable catalyst for regioselective ring opening of epoxides. RSC Adv 2012;2:3321.

Jones B, Moody GJ, Thomas JR. N-iodopyridinium dichloroiodate(I). Inorg Chem 1970;9:114–9.

Nguyen HT, Nguyen DD, Spanget-Larsen J. Ionic reaction products of iodine with pyridine, 4-methylpyridine, and 4-tert-butylpyridine in a polyethylene matrix. A FTIR polarization spectroscopic investigation. Chem Phys Lett 2019;716:119–25.

Reid C, Mulliken RS. Molecular Compounds and Their Spectra. IV. The Pyridine-Iodine System 1. J Am Chem Soc 1954;76:3869–74.

Tassaing T, Besnard M. Ionization Reaction in Iodine/Pyridine Solutions: What Can We Learn from Conductivity Measurements, Far-Infrared Spectroscopy, and Raman Scattering? J Phys Chem A 1997;101:2803–8.

Yadav J, SubbaReddy B, Gayathri K, Meraj S, Prasad A. Bismuth(III) Triflate Catalyzed Condensation of Isatin with Indoles and Pyrroles­: A Facile Synthesis of 3,3-Diindolyl- and 3,3-Dipyrrolyl Oxindoles. Synthesis (Stuttg) 2006;2006:4121–3.

Varun, Sonam, Kakkar R. Isatin and its derivatives: a survey of recent syntheses, reactions, and applications. Medchemcomm 2019;10:351–68.

Nain S, Mathur G, Anthwal T, Sharma S, Paliwal S. Synthesis, Characterization, and Antibacterial Activity of New Isatin Derivatives. Pharm Chem J 2023:1–8.

Subba Reddy BV, Rajeswari N, Sarangapani M, Prashanthi Y, Ganji RJ, Addlagatta A. Iodine-catalyzed condensation of isatin with indoles: A facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity. Bioorg Med Chem Lett 2012;22:2460–3.

Downloads

Published

2023-09-06

How to Cite

JOHARI, S., & KHALIGH, N. G. (2023). Poly(4-vinylpyridine)iodonium triiodide: A new efficient catalyst for the synthesis of 3,3-diheteroaromatic oxindole analogues. Malaysian Catalysis-An International Journal, 3(1). Retrieved from https://mcij.um.edu.my/index.php/MCIJ/article/view/44549

Issue

Vol. 3 No. 1 (2023)

Section

Articles