Lactic acid as a new, green and efficient catalyst for one-pot four-component synthesis of bis-phenantroimidazoles based on 4,4’-diamino diphenyl ether
Subject Areas : Others
Samaneh Samsami
1
,
Seyed Mahdi Saadati
2
,
Fatemeh Rashedi Sani
3
1 - Department of Chemistry, Faculty of Sciences, Bojnourd Branch, Islamic Azad University, Bojnourd, Iran
2 - Department of Chemistry, Faculty of Sciences, Bojnourd Branch, Islamic Azad University, Bojnourd, Iran
3 - Department of Chemistry, Faculty of Sciences, Bojnourd Branch, Islamic Azad University, Bojnourd, Iran
Keywords: Bis-Phenanthroimidazole, 4, 4’- diamino diphenyl ether, Lactic acid, Green catalyst.,
Abstract :
Imidazoles are the most important group of the nitrogen containing heterocyclic compounds and core of many of the biological systems which have a wide range of medicinal and biological properties. In the present research, for the first time, bis-phenanthroimidazole derivatives were synthesized via one-pot four-components reaction of aromatic aldehyde, 4,4’- diamino diphenyl ether, 9,10-phenanthrenequinone and ammonium acetate in the presence of lactic acid as catalyst. In order to investigate the effect of lactic acid as a catalyst in the synthesis of bis-phenantroimidazole derivatives and to find the optimal conditions, first one derivative was selected as a model reaction and the effect of different conditions, including the optimal amount of the catalyst, the optimal conditions with or without solvent, and temperature were investigated. Then other derivatives were synthesized in optimal conditions. The advantages of this method are high yield, less reaction time, easier separation and the use of an environmentally friendly catalyst.
1. United States Environmental Protection Agency. Green Chemistry. 206 (2013).
2. Martinez, F. A. C.; Balciunas, E. M.; Salgado, J. M.; González, J. M. D.; Converti, A.; Oliveira, R. P. S., Lactic acid properties, applications and production, A review. Trends in Food Science & Technology. (2020). 30, 70.
3. M. Fatahpour, N. Hazeri, MT. Maghsoodlou, M. Lashkari, Polycyclic Aromatic Compounds, 39, 311 (2019).
4 . حذرخانی، ح. لاکتیک اسيد يك كاتاليزگر زيست تخريب پذير و موثر براي تراكم كلايزن – اشميت در شرايط واكنش بدون حلال، شیمی سبز و فناوری‌های پایدار، 8، 9 (1400).
5. سعادتی،س.م، بحری، س.ن. سنتز سبز مشتقات بنزوکسازول در حلال آب و در حضور لاکتیک اسید به عنوان کاتالیزور ارزان و
دوست‌دار محیط زیست، شیمی سبز و فناوری‌های پایدار، 15، 54 (1402).
6. N.Hazeri, M. Lashkari, H. Faroughi Niya, H.Pourbalouch, J. Appl. Chem. Res. 14, 51 (2020).
7. M.Kangani, N. Hazeri, A Yazdani-Elah-Abadi, M.T. Maghsoodlou, Polycyclic Aromatic Compounds, 38, 322 (2018).
8. F. Noori Sadeh, N. Hazeri, M.T. Maghsoodlou, M. Lashkari, Organic Preparations and Procedures International, 49, 35 (2017).
9. P. Gupta, K. Jitendra. Int. J. Modern Chem.7 (2), 60 (2015).
10.H.Fujioka,K.Murai,Y.Ohba, A.Hiramatsu, Y.Kita. Tetrahedron Lett. 46 , 2197 (2005).
11.HM.Rolfe. J. cosmetic dermatology. 13, 324 (2014).
12.GJ.Griffith,sMB.Hauck,R.Imwinkelried, J.Kohr ,CA. Roten, GC.Stucky, et al. J. of org. chem. 64, 8084 (1999).
13. F. R. Japp, F. W. Streatfield, J. Chem. Soc., 41, 146 (1882).
14. N. Pourmorteza, M. Ariannezhad, H. Behmadi, Z. Amini Moghaddam, Organic
Preparations and Procedures International 54.79 (2022(.
15. G.G. Dias, M. O. Rodrigues, E. R. S. Paz, M. P. Nunes, M. H. Araujo, F.S. Rodembusch, E. N. da Silva Júnior, ACS sensors 7, 2865 (2022).
16.S.M. Saadati, M.H. Mosslemin, H. Behmadi, A. Shams, J. Chem. Res. 15, 487 (2013).