POTASSIUM 2-OXOIMIDAZOLIDINE-1,3-DIIDE AS A NOVEL CATALYST FOR GRIND SYNTHESIS OF PYRANO[4,3-b]CHROMENONE
- Potassium 2-oxoimidazolidine-1,
- 3-diide,
- pyrano[4,
- 3-b]chromenes,
- 4-hydroxycoumarin
- β-naphthol ...More
Copyright (c) 2019 Journal of the Chilean Chemical Society
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Abstract
A novel, clean, mild and eco-friendly benign route to pyrano[4,3-b]chromenes through cyclocondensation reaction of β-naphthol, aldehydes and 4-hydroxycoumarin, using POImD as a novel and reusable organometallic catalyst, is described. The present methodology offers several advantages such as simple work-up procedure, short reaction time, high yields of product with better purity and green aspect by avoiding toxic catalyst and hazardous solvent. All of synthesized compounds were characterized by IR, NMR and elemental analyses.
References
- (a). H. Miao, Z. Yang, Org. Lett. 2, 1765, (2000); (b). A. Akbari, A. Hosseini-Nia, Iranian J. Org. Chem. 6, 1183, (2014).
- (a). P. Kumar, M. S. Bodas, Org. Lett. 2, 3821, (2000); (b). N. Thomas, S. M. Zachariah Asian J. Pharm. Clinic. Res. 6, 11, (2013).
- T. A. Bayer, S. Schafer, H. Breyh, O. Breyhan, C. Wirths, G. A. Treiber, Multhaup, Clin Neuropathol. 25, 163, (2006).
- (a). B. M. Trost, Chem. Int. Ed. Engl. 34, 259, (1995); (b). M. El-Agrody, A. M. Fouda, E. S. A. E. H. Khattab, Med. Chem. Res. 22, 6105, (2013).
- Sh. Jain, P. K. Paliwal, G. N. Babu, A. Bhatewara, J. Saudi Chem. Soc. 18, 535, (2014).
- A. M. M. El-Saghier, M. B. Naili, B. K. Rammash, N. A. Saleh, K. M. Kreddan, Arkivoc xvi 83, (2014).
- W. O. Foye, Principidi Chimica Farmaceutica Piccin- Padova, 1991, Italy.
- E. A. A. Hafez, M. H. Elnaghi, A. G. A. Elagamey, F. M. A. A. El-Taweel, Heterocycles. 26, 903, (2004).
- A. Bolognese, G. Correale, M. Manfra, A. Levecchia, O. Mazzoni, E. Novellino, P. Lacolla, G. Sanna, R. Loddo, J. Med. Chem. 47, 849, (2004).
- (a). G. P. Ellis, The Chemistry of Heterocyclic Compounds. In Chromenes; Chromenes, and Chromenes; Weissberger; Taylor, A.; Eds, E. C.; John Wiley; NewYork. Chapter 2, 11, (1977); (b). M. Kidwai, S. Saxen, M. K. R. Khan, S. S. Thukral, Bioorg. Med. Chem. Lett. 15, 4295, (2005).
- T. Hanamoto, K. Shindo, M. Matsuoka, Y. Kiguchi, M. Kondo, J. Chem. Soc., Perkin Trans. 1, 3082, (2000).
- P. T. Kaye, X. W. Nocanda, J. Chem. Soc., Perkin Trans. 1, 1331, (2000).
- H. H. Jardosh, M. P. Patel, Med. Chem. Res. 22, 905, (2012).
- K. A. Parker, T. L. Mindt, Org. Lett. 3, 3875, (2001).
- B. V. S. Reddy, S. Jalal, P. Borkar, J. S. Yadav, P. P. Reddy, A. C. Kunwar, B. Sridhar, Org. Biomol. Chem. 10, 656, (2012).
- S. Chang, R. H. Grubbs, J. Org. Chem. 63, 864, (1998).
- (a) Q. Wang, M. G. Finn, Org. Lett. 2, 4063, (2000); (b) G. W. Kabalka, B. Venkataiah, B. C. Das, Synlett. 2194, (2004).
- M. Iyer, G. R. Trivedi, Synth. Commun. 20, 1347, (1990).
- R. S. Varma, R. Dahiya, J. Org. Chem. 63, 8038, (1998).
- J. Hlubucek, E. Ritchie, W. C. Taylor, Tetrahedron Lett. 10, 1369, (1969).
- L. W. Ye, X. L. Sun, C. Y. Zhu, Y. Tang, Org. Lett. 8, 3853, (2006).
- U. M. Lindstrom, Chem. Reviews, 102, 2751, (2002).
- Z. B. Xu, J. Qu, Chem. A Euro. J. 19, 314, (2013).
- S. Chitra, N. Paul, S. Muthusubramanian, P. Manisankar, Green Chem. 13, 2777, (2011).
- M. Nikpassand, L. Zare Fekri, M. R. Mousavi, Lett. Org. Chem. 9, 375, (2012).
- M. Nikpassand, M. Mamaghani, F. Shirini, K. Tabatabaeian, Ultrason. sonochem. 17, 301, (2010).
- M. Nikpassand, L. Zare Fekri, M. Gharib, O. Marvi, Lett. Org. Chem. 9, 745, (2012).
- M. Nikpassand, D. Pirdelzendeh, Dyes Pig. 130, 314, (2016).
- H. Kiyani, F. Ghorbani, Jordan J. Chem. 9, 1, (2014).
- X. Wang, G. Lu, F. Yan, W. Ma, L. Wu, J. Hetero. Chem. 48, 1379, (2011).
- Y. Wan, C. Wang, H. Wang, L. Zhao, X. X. Zhang, J. J. Shi, S. Huang, G. X. Liu, H. Wu, J. Heterocyclic Chem. 51, 1293, (2014).
- W. Ma, X. Wang, F. Yan, L. Wu, Y. Wang, Monatshefte fur Chemie, 142, 163, (2011).