Issue

Vol. 25 No. 4 (2013): Vol 25 Issue 4

Copyright (c) 2013 AJC

Creative Commons License

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

One-Pot Multi Component Synthesis of Xanthenediones and Acridinediones at Room Temperature

https://doi.org/10.14233/ajchem.2013.13260
Hamid Reza Safaei
Department of Applied Chemistry, Faculty of Science, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran
Abolfazl Eshghi Movahhed
Department of Applied Chemistry, Faculty of Science, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran
Mansooreh Davoodi
Department of Applied Chemistry, Faculty of Science, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran
Mohsen Shekouhy
Department of Applied Chemistry, Faculty of Science, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran ; Young Researchers Club, Shiraz Branch, Islamic Azad University, Shiraz, Iran
Vahid Rahmanian
Department of Industrial Polymer Engineering, Shiraz Branch, Islamic Azad University, Shiraz, Iran
Maryam Safaei
Department of Industrial Polymer Engineering, Shiraz Branch, Islamic Azad University, Shiraz, Iran

Corresponding Author(s) : Hamid Reza Safaei

hrs@iaushiraz.net; hrsafaei@yahoo.com

Asian Journal of Chemistry, Vol. 25 No. 4 (2013): Vol 25 Issue 4

Abstract

A facile and efficient protocol for the synthesis of xanthenedione and acridinrdione derivatives has been developed via the one-pot condensation reaction between dimedone and aldehydes (for the synthesis of xanthenediones) and dimedone, aldehydes and primary amines (for the synthesis of acridinediones) in presence of the formic acid as solvent at room temperature. All the products were obtained in good to excellent yields and all reactions were completed in short times.

Keywords

Xanthenedione Acridinediones Formic acid Multi component reactions
Reza Safaei, H., Eshghi Movahhed, A., Davoodi, M., Shekouhy, M., Rahmanian, V., & Safaei, M. (2012). One-Pot Multi Component Synthesis of Xanthenediones and Acridinediones at Room Temperature. Asian Journal of Chemistry, 25(4), 1981–1984. https://doi.org/10.14233/ajchem.2013.13260
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. (a) J. Zhu and H. Bienayme, Multi Component Reactions, Wiley-VCH: Weinheim, Germany (2005); (b) L.F. Tietze, G. Brasche and K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH: Weinheim, Germany (2006); (c) U. Domling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000); (d) E. Soleimani, M.M. Khodaei, N. Batooie and M. Baghbanzadeh, Green Chem., 13, 566 (2011).
  2. (a) S.B. Krasnoff, D. Faloon, J.E. Williams and D.M. Gibson, Biocontrol. Sci. Technol., 9, 215 (1999); (b) H. Wang, L. Lu, S. Zhu, Y. Li and W. Cai, Curr. Microbiol., 52, 1 (2006); (c) Y.F. Qiao, T. Okazaki, T. Ando, K. Mizoue, K. Kondo, T. Eguchi and K. Kakinuma, J. Antibiot., 51, 282 (1998); (d) S. Limsuwan, E.N. Trip, T.R.H.M. Kouwen, S. Piersmam,A. Hiranrat, W. Mahabusarakam, S.P. Voravuthikunchai, J.M. vanDijl and O. Kayser, Phytomedicine, 16, 645 (2009).
  3. J.P. Poupelin, G. Saintruf, J.C. Perche, J.C. Roussey, B. Laude, G. Narcisse, F. Bakrilogeais and F. Hubert, Eur. J. Med. Chem., 15, 253 (1980).
  4. J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison and C. Tsai, Cell Biol. Int. Rep., 14, 1075 (1990).
  5. S. Hatakeyama, N. Ochi, H. Numata and S. Takano, Chem. Commun., 17, 202 (1998).
  6. Y.M. Shchekotikhin and T.G. Nikolaeva, Chem. Heterocycl. Compd., 1, 32 (2006).
  7. J. Kinjo, H. Uemura, T. Nohara, M. Yamashita, N. Marubayashi and K. Yoshihira, Tetrahedron Lett., 36, 5599 (1995).
  8. E. Antman, J. Muller, S. Goldberg, R. Macalpin, M. Ruben-fire, B. Tabatznik, C. Liang, F. Heupler, S. Achuff, N. Reichek, E. Geltman, N.Z. Kerin, R.K. Neff and E. Raunwald, N. Engl. J. Med., 302, 1269 (1980).
  9. (a) M. Guazzi, M. Olivari, A. Polese, C. Fiorentini, F. Margrini and P. Moruzzi, Clin. Pharmacol. Ther., 22, 528 (1977); (b) R.S. Hornung, B.A. Gould, R.I. Jones, T.N. Sonecha and E.B. Raferty, Am. J. Cardiol., 51, 1323 (1983).
  10. E. Delfourne, C. Roubin and J. Bastide, J. Org. Chem., 65, 5476 (2000).
  11. J. Antonini, P. Polucci, A. Magnano and S. Martelli, J. Med. Chem., 44, 3329 (2001).
  12. M.G. Ferlin, C. Marzano, G. Chiarelotto, F. Baccichetti and F. Bordin, Eur. J. Med. Chem., 827 (2000).
  13. X. Fan, X. Hu, X. Zhang and J. Wang, Can. J. Chem., 83, 16 (2005).
  14. T.S. Jin, J.-S. Zhang, A.-Q. Wang and T.-S. Li, Synth. Commun., 35, 2339 (2005).
  15. F. Darviche, S. Balalaie, F. Chadegani and P. Salehi, Synth. Commun., 37, 1059 (2007).
  16. T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang and T.S. Li, Synlett, 866 (2004).
  17. G. Song, B. Wang, H. Luo and L. Yang, Catal. Commun., 8, 673 (2007).
  18. B. Das, P. Thirupathi, I. Mahender, K.R. Reddy, B. Ravikanth and L. Nagarapu, Catal. Commun., 8, 535 (2007).
  19. M. Seyyedhamzeh, P. Mirzaei and A. Bazgir, Dyes Pigments, 76, 836 (2008).
  20. H.N. Karade, M. Sathe and M. P. Kaushik, Arkivoc, 252 (2007).
  21. S. Kantevari, R. Bantu and L. Nagarapu, Arkivoc, 136 (2006).
  22. K. Niknam and M. Damya, J. Chin. Chem. Soc., 56, 659 (2009).
  23. A. Sharifi, M.S. Abaee, A. Tavakkoli, M. Mirzaei and A. Zolfaghari, Synth. Commun., 38, 2958 (2008).
  24. G.H. Mahdavi, M.A. Bigdeli and Y. Saeidi Hayeniaz, Chin. Chem. Lett., 20, 539 (2009).
  25. E.C. Horning and M.G. Horning, J. Org. Chem., 11, 95 (1946).
  26. K. Niknam, F. Panahi, D. Saberi and M. Mohagheghnejad, J. Heterocycl. Chem., 47, 292 (2010).
  27. B. Das, P. Thirupathi, I. Mahender, V.S. Reddy and Y.K. Rao, J. Mol. Catal. A: Chem., 247, 233 (2006).
  28. K. Venkatesan, S.S. Pujari and K.V. Srinivasan, Synth. Commun., 39, 228 (2009).
  29. M. Dabiri, M. Baghbanzadeh and E. Arzroomchilar, Catal. Commun., 9, 939 (2008).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 1