Iodine-promoted oxidative cyclization for green synthesis of 2-arylquinazolin-4(3H)-ones in polyethylene glycol (PEG)

Document Type : Original Article

Authors

1 CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran

2 Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Abstract

A metal-free and iodine promoted oxidative system for cyclization of primary benzyl amines with anthranilamide to afford 2-arylquinazolin-4(3H)-ones in PEG-400 as a green, inexpensive, non-toxic and reusable solvent medium has been developed.

Keywords

Main Subjects

References

[1]      (a) Chen, J.; Spear, S. K.; Huddleston, J. G. & Rogers, R. D. (2005). Green Chem., 7, 64.; (b) Colacinoa, E.; Martineza, J.; Lamatya, F.; Patrikeevaa, L. S.; Khemchyanb, L. L.; Ananikovb, V. P. & Beletskayac, I. P. (2012). Coord. Chem. Rev., 256, 2893.
[2]      Bailey Jr. F. E.; & Koleske, J. V. (1976). Poly(ethylene oxide), Academic Press, New York.
[3]      Lüth, A. & Löwe, W. (2008). Eur. J. Med. Chem., 43, 1478.
[4]      Kuarm, B. S.; Reddy, Y. T.; Madhav, J. V.; Crooks, P. A. & Rajitha, B. (2011). Bioorg. Med. Chem. Lett., 21, 524.
[5]      Kenichi, O.; Yoshihisa, Y.; Toyonari, O.; Toru, I. Yoshio, I. (1985). J. Med. Chem., 28, 568.
[6]      Aly, M. M.; Mohamed, Y. A.; El-Bayouki, K. A. M.; Basyouni, W. M. & Abbas, S. Y. (2010). Eur. J. Med. Chem., 45, 3365.
[7]      Tereshima, K.; Shimamura, H.; Kawase, A.; Tanaka, Y.; Tanimura, T.; Kamisaki, T.; Ishizuka, Y. & Sato, M. (1995). Chem. Pharm. Bull., 43, 2021.
[8]      (a) Bedi, P. M. S.; Kumar, V. & Mahajan, M. P. (2004). Bioorg. Med. Chem. Lett., 14, 5211. (b) Meyyanathan, S. N.; Ramu, M. & Suresh, B. (2010). Med. Chem. Res., 19, 993.
[9]      Malamas, M. S. & Millen, J. (1991). J. Med. Chem., 34, 1492.  
[10]    Li, H.; Huang, R.; Qiu, D.; Yang, Z.; Liu, X.; Ma, J. & Ma, Z. (1998). Prog. Nat. Sci., 8, 359.
[11]    (a) Chawla, A. & Batra, C. (2013). Int. Res. J. Pharm., 4, 49.; (b) Arora, R.; Kapoor, A.; Gill, N. S. & Rana, A. C. (2011). Int. Res. J. Pharm., 2, 22.
[12]    (a) Mekala, R.; Akula, R.; Kamaraju, R. R.; Bannoth, C. K.; Regati, S. & Sarva, J. (2014). Synlett, 25, 821. (b) Cheng, R.; Guo, T.; Zhang-Negrerie, D.; Du, Y. & Zhao, K. (2013). Synthesis, 45, 2998. (c) Romero, A. H.; Salazar, J. & López, S. E. (2013). Synthesis, 45, 2043. (d) Zhou, J.; Fu, L.; Lv, M.; Liu, J.; Pei, D. & Ding, K. (2008). Synthesis, 24, 3974. (e) Zheng, Z. & Alper, H. (2008). Org. Lett., 10, 829.
[13]    (a) Wei, H.; Li, T.; Zhou, Y.; Zhou, L. & Zeng, Q. (2013). Synthesis, 45, 3349. (b) Xu, W.; Jin, Y.; Liu, H.; Jiang, Y. & Fu, H. (2011). Org. Lett., 13, 1274. (c) Qi, X. X.; Song, Z. Z.; Gong, J. L.; Fang, Z. Y. & Wu, X. F. Chin. Chem. Lett., 27, 21.
[14]    (a) Tashrifi, Z.; Rad-Moghadama, K.; Mehrdad, M.; Soheilizad, M.; Larijani, B. & Mahdavi, M. (2018). Tetrahedron, 59, 1555. (b) Asgari, M. S.; Soheilizad, M.; Ranjbar, P. R.; Larijani, B.; Rahimi, R.  Mahdavi, M. (2019). Tet. Lett., 60, 583. (c) Allahabadi, E.; Ebrahimi, S.; Soheilizad, M. Khoshneviszadeh, M. Mahdavi, M. (2017). Tet. Lett., 58, 121.
Frontiers in Chemical Research
Volume 1, Issue 1 - Serial Number 1
September 2019
Pages 13-16

Files

History

  • Receive Date: 17 June 2019
  • Revise Date: 26 June 2019
  • Accept Date: 30 July 2019

Share

How to cite

Statistics