Iodine supported poly(4-vinylpyridine): Efficient and recoverable catalyst for the synthesis of 3,3-diheteroaromatic oxindoles

Authors

  • Dr. Nader Ghaffari Khaligh Nanotechnology and Catalysis Research Center, Institute for Advanced Studies (IAS), Universiti Malaya, 50603, ‎Kuala Lumpur, Malaysia
  • Fathiy Mutalabisin Nanotechnology and Catalysis Research Center, Institute for Advanced Studies (IAS), Universiti Malaya, 50603, ‎Kuala Lumpur, Malaysia

Keywords:

Iodine, Poly(4-vinylpyridine), 3,3-Diheteroaromatic oxindole, Solvent-free, Green chemistry

Abstract

An efficient methodology for the synthesis of 3,3-diheteroaromatic oxindole derivatives has been demonstrated by coupling indole-2,3-dione (isatin) with differently substituted indoles and pyrrole in the presence of iodine-supported on poly(4-vinylpyridine) under neutral and solvent-free conditions. The products were obtained in a short time and good to excellent yields.

Downloads

Download data is not yet available.

References

Jereb, M.; Vražič D.; Zupan, M. Acta Chim. Slov. 2009, 56, 652.

Jereb, M.; Zupan M.; Stavber, S.Chem. Commun. 2004, 2614.

Vaino A. R.; Szarek, W. A. Adv. Carbohydr. Chem. Biochem. 2001, 56, 9.

Biswas, A.; Selling, G. S.; Shogren, R. L.; Willett, J. L.; Buchanan, C. M.; Cheng, H. N. Chem. Today. 2009, 27, 33.

Wang, H.-S.; Miao, J.-Y.; Zhao, L.-F. Chin. J. Org. Chem. 2005, 25, 615.

Zhang, Z.; Liu, Q. Progress Chem. 2006, 18, 270.

Shen, S.; Xu, X.; Ji, S. Chin. J. Org. Chem. 2009, 29, 806.

Zhou, Y.; Yan, P.; Li, G.; Chen, Z. Chin. J. Org. Chem. 2009, 29, 1719.

Banerjee, A. K.; Vera, W.; Mora, H.; Laya, M. S.; Bedoya, L.; Cabrera, E. V. J. Sci. Ind. Res. 2006, 65, 299.

Das, S.; Borah, R.; Devi, R. R.; Thakur, A. J. Synlett. 2008, 2741.

French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354.

Mphahlele, M. J. Molecules. 2009, 14, 4814.

Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.

Mphahlele, M. J. Molecules.2009, 14, 5308.

Stavber, S.; Jereb, M.; Zupan, M. Synthesis. 2008, 1487.

Podgoršek, A.; Zupan, M.; Iskra, J. Angew. Chem., Int. Ed. 2009, 48, 8424.

(a) Joshi, K. C.; Pathak, V. N.; Jain, S. K. Pharmazie 1980, 35, 677; (b) Bolotov, V. V.; Drugovina, V. V.; Yakovleva, L. V.; Bereznyakova, A. I. Khim. Farm. Zh. 1982, 16, 58; (c) Pajouhesh, H.; Parsons, R.; Popp, F. D. J. Pharm. Sci. 1983, 72, 318; (d) Popp, F. D. J. Heterocyclic Chem. 1984, 21, 1367; (e) Garrido, F.; Ibannez, J.; Gonalons, E.; Giraldez, A. Eur. J. Med. Chem. 1975, 10, 143; (f) Fensome, A.; Zhang, P.; Marci, C.; Wrobel, J. E.; Melenski, E. G.; Zhi, L.; Jones, T. K.; Tegley, C. M.; Edwards, J. P. U. S. Patent 2005, 6841568.

Kamano, Y.; Zhang, H. P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783.

Bhowal, S. K.; Lala, S.; Hazra, A.; Paira, P.; Banerjee, S.; Mondal, N. B.; Chakrabarty, S. Contraception 2008, 77, 214.

Paira, P.; Hazra, A.; Kumar, S.; Paira, R.; Sahu, K. B.; Naskar, S.; Saha, P.; Mondal, S.; Maity, A.; Banerjee, S.; Mondal, N. B. Bioorg. Med. Chem. Lett. 2009, 19, 4786.

(a) Klumpp, D. A.; Yeung, K. Y.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1998, 63, 4481; (b) Franklin, D. P. Ger. Patent, 2258505, 1973.; (c) Jursic, B.; Stevens, E. D. Tetrahedron Lett. 2002, 43, 5681.

(a) Azizian, J.; Mohammadi, A. A.; Karimi, N.; Mohammadizadeh, M. R.; Karimi, A. R. Catal. Commun. 2006, 7, 752; (b) Wang, S. Y.; Ji, S. J. Tetrahedron 2006, 62, 1527; (c) Yadav, J. S.; Reddy, B. V. S.; Gayathri, K. U.; Meraj, S.; Prasad, A. R. Synthesis 2006, 4121.

Downloads

Published

2023-09-06

How to Cite

Khaligh, D. N. G., & Mutalabisin, F. . (2023). Iodine supported poly(4-vinylpyridine): Efficient and recoverable catalyst for the synthesis of 3,3-diheteroaromatic oxindoles. Malaysian Catalysis-An International Journal, 3(1). Retrieved from http://jummec.um.edu.my/index.php/MCIJ/article/view/41722

Issue

Section

Articles