Issue

Vol. 25 No. 5 (2013): Vol 25 Issue 5

Copyright (c) 2013 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

A Green and Facile Synthesis of 2-Alkylsulfanyl-3H-quinazolin-4-one

https://doi.org/10.14233/ajchem.2013.13593
B. Srinivasa Reddy
Department of Chemistry, J.N.T. University, Hyderabad, College of Engineering, Kukatpally, Hyderabad-500 085, India
A. Naidu
Department of Chemistry, J.N.T. University, Hyderabad, College of Engineering, Kukatpally, Hyderabad-500 085, India
P.K. Dubey
Department of Chemistry, J.N.T. University, Hyderabad, College of Engineering, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : B. Srinivasa Reddy

srinivasjntu123@gmail.com

Asian Journal of Chemistry, Vol. 25 No. 5 (2013): Vol 25 Issue 5

Abstract

Reaction of 2-thioquinazolinone (1) with various alkylating agents like dimethyl sulphate, diethyl sulphate and benzyl chloride in the presence of K2CO3 as a mild base, by a simple physical grinding, microwave irradiation and PEG-600 under solvent-free conditions for 10-15 min at room temperature, followed by processing, gave respectively 2-methylsulfanyl-3H-quinazolin- 4-one (2a, i.e., R = CH3), 2-ethylsulfanyl-3H-quinazolin-4-one (2b, i.e., R = C2H5) and 2-benzyl sulfanyl-3H-quinazolin-4-one (2c, i.e., R = PhCH2Cl). It appears from this study that green syntheses such as solid phase synthesis (physical grinding) and microwave irradiation gives better yields, quality and in less reaction time the products over conventional methods involving green solvents like ethanol, PEG-600 etc. The entire sequences of reactions have been carried out using eco-friendly solvents and green conditions.

Keywords

2-Thioquinazolinone Alkylating agent (DMS/DES/PhCH2Cl) PEG-600 Ethanol K2CO3 M.W
Srinivasa Reddy, B., Naidu, A., & Dubey, P. (2012). A Green and Facile Synthesis of 2-Alkylsulfanyl-3H-quinazolin-4-one. Asian Journal of Chemistry, 25(5), 2644–2646. https://doi.org/10.14233/ajchem.2013.13593
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. M. Alagarasamy, S. Meena, R.S. Vijaya Kumar and K.V. Ramesh, ARKIVOC, 149 (2006).
  2. K. Ozaki, Y. Yamada, T. Oine, T. Ishizuka and Y. Iwasawa, J. Med. Chem., 28, 568 (1985).
  3. G. Bonola Dare, P. Mgistretti, S. Massarani and I. Setnikar, J. Med. Chem., 11, 1136 (1968).
  4. H.J. Hess, T.H. Cronin and A. Scriabine, J. Med. Chem., 11, 140 (1968).
  5. P.N. Bhargava and M.R. Chaurasia, J. Med. Chem., 11, 140 (1968).
  6. P.S.N. Reddy, G.K. Venugopal Rao and P.N.S. Pai, Indian J. Heterocyc. Chem., 16, 243 (2007).
  7. E.L. Badaway, A.M. Syed, M. Rida, F.S.G Sliman and T. Thomas, Monatsh. Chem., 120, 1159 (1989).
  8. V. Murgan, C. Thomas, G.V.S. Ramasarma and E.P. Kumar, Indian J. Pharm. Sci., 65, 386 (2003).
  9. S.S. Caroll, M.J. Stahohurt and D.B. Oslen, Biol. Sci., 269, 3251 (1994).
  10. A. Guersoy and N. Illhan, IL Farmaco, 50, 559 (1995).
  11. D. Pandeya, G. Sriram and E. Clerck, Pharm. Acta. Helv., 74, 11 (1999).
  12. G. Grover and S.G. Kini, Eur. J. Med. Chem., 41, 256 (2006).
  13. J. Kunes, J. Bazant, M. Pour, K. Waisser, M. Slosarek and J. Janota, IL Farmaco, 55, 725 (2000).
  14. W. Waiser, O. Burer, P. Holy, J. Kunes, R. Oswald, L. Jirasakova, M. Pour, V. Klimesova, K.J. Palat, H. Kaustova, M. Danese and U. Mollamann, Pharmazie, 58, 1137 (2003).
  15. P.M. Chandrika, T. Yakaiah, A.R.R. Rao, B. Narasiah, N.C. Reddy, V. Sridhar and J.V. Rao, Eur. J. Med. Chem., 43, 846 (2008).
  16. S.L. Cao, Y.P. Feng, Y.V. Jiang, S.Y. Liu, G.Y. Ding and R.T. Li, Biorg. Med. Chem. Lett., 15, 1915 (2005).
  17. M.A.H. Ismail, S. Barker, D.A. Abouelella, K.A.M. Aouzid, R.A. Toubar and M.H. Todd, J. Med. Chem., 49, 1526 (2006).
  18. K.M. Shakhadoyatov, S. Yangibaev, L.M. Yun and C.S. Kadirov, Chem. Nat. Comp., 18, 106 (1982).
  19. Z. Szabo, O. Erzsebet and T. Lorand, J. Biochem. Biophys. Methods, 61, 77 (2004).
  20. M. Venkatanarayana and P.K. Dubey, Green Chem. Lett. Rev., 3, 257 (2010).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0