Abstract
A rapid and efficient solvent-free one-pot synthesis of coumarin derivatives by Pechmann condensation reactions of phenols with ethyl acetoacetate using FeF3 as a catalyst under microwave irradiation is described. This one-pot synthesis on a solid inorganic support provides the products in good yields. The newly synthesized compounds were systematically characterized by IR, 1H-NMR, 13C-NMR, MS and elemental CHN analyses. The proposed solvent-free microwave irradiation method using the environmentally friendly catalyst FeF3 offers the unique advantages of high yields, shorter reaction times, easy and quick isolation of the products, excellent chemoselectivity, and a one-pot, green synthesis. The products were screened for antimicrobial activity, and the results showed that the compounds reacted against all the tested bacteria.
Highlights
Coumarin and its derivatives are biologically and pharmacologically active compounds with a wide range of properties as antitumor, antimicrobial, anti-HIV, anticoagulant, anti-inflammatory and antioxidant agents [1,2]
Coumarin derivatives are typically synthesized by chemical modification of the coumarin ring
Owing to their diverse pharmacological properties and natural sources of origin, coumarins play an important role in the synthesis of natural products [5,6,7]
Summary
Coumarin and its derivatives are biologically and pharmacologically active compounds with a wide range of properties as antitumor, antimicrobial, anti-HIV, anticoagulant, anti-inflammatory and antioxidant agents [1,2]. Several improved synthetic methodologies have been developed that use a variety of Lewis acid catalysts [9,10,11,12], phase transfer catalysts [13,14,15,16,17], microwave reactions [18], and molecular iodine [19]. Some of these methods are expensive, environmentally unfriendly, produce low yields, are incompatible with other functional groups, and involve labor-intensive product isolation procedures. Several methods, including Perkin [20], Knoevenagel [21], Reformatsky [22], Wittig [23], and Pechmann [24] reactions, have been adopted for the synthesis of coumarins
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