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| کلمات کلیدی | METAL-FREE FRIEDEL-CRAFTS ACYLATION OF AROMATIC COMPOUNDS AT ROOM TEMPERATURE ETHYLENEDIAMMONIUM FORMATE IONIC LIQUID Adibi Hadi, Gorgin-Karaji Yousef, and Asgharlou Hadi Department of Medicinal Chemistry, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah 67145-1673, IR Iran E-mail: hadibi@kums.ac.ir The Friedel-Crafts acylation of aromatic compounds is an important method for the synthesis of aromatic ketones.1 This method has been widely used in the synthesis of pharmaceuticals, fine chemicals and polymers.2 The acylation reaction involves substitution by an acyl group, derived from a carboxylic acid derivative, usually an acid halide or acid anhydride. The carbonyl group in such acid derivatives is sufficiently basic that formation of a complex requires a strong Lewis acid. Generally, Lewis acids such as BF3, ZnCl2, TiCl4, SbF5, etc., could promote this reaction; however, AlCl3 is most commonly used as catalyst. Although, this reaction is widely applied in industry, there are some disadvantages such as long reaction time, troublesome product recovery and purification, catalysts can not be reused and formation of environmentally hazardous, corrosive aluminate waste. In recent years, room temperature ionic liquids (ILs) have shown great promise as an attractive alternative to conventional solvents. One of several advantages of ionic liquids is that they are environmentally benign since they have no detectable vapor pressure. As a result of their green credentials and potential to enhance rate and selectivity, ionic liquids are finding increasing applications in organic synthesis.3 There are plethora literature examples reporting improved reaction characteristics of the Friedel-Crafts acylation in ILs.4-6 In this project, we will report the Friedel-Crafts acylation of aromatic compounds with acetic anhydride as an acylating agent in ethylenediammonium formate as a novel ionic liquid (Scheme 1). Scheme 1 1. Olah, G. A. Friedel-Crafts Chemistry, Wiley, New York, 1973. 2. Kozhevnikov, I. V. Appl. Catal., A: General, 2003, 256, 3. 3. Welton, T. Chem. Rev. 1999, 99, 2071. 4. Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219. 5. Yeung, K.-S.; Farkas, M. E.; Qiu, Z.; Yang, Z. Tetrahedron Lett. 2002, 43, 5793. 6. Ross, J.; Xiao, J. Green Chem. 2002, 4, 129. |
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