Microwave Assisted Convenient One-Pot Synthesis of Coumarin Derivatives via Pechmann Condensation Catalyzed by FeF3 under Solvent-Free Conditions and Antimicrobial Activities of the Products

Abstract

Abstract:A rapid and efficient solvent-free one-pot synthesis of coumarin derivatives by Pechmann condensation reactions of phenols with ethyl acetoacetate using FeF 3 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, 1 H-NMR, 13 C-NMR, MS and elemental CHN analyses. The proposed solvent-free microwave irradiation method using the environmentally friendly catalyst FeF 3 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.

Zirconia-based catalyst for the one-pot synthesis of coumarin through Pechmann reaction

“… Temperature (°C) Solvent Yield References 1 Zeolite BEA 240 130 PhNO 2 63 [ 29 ] 2 PFPAT 180 110 Toluene 90 [ 30 ] 3 MFRH 50 80 S.F. 65 [ 30 ] 4 Nanoreactors 60 130 S.F. 30 [ 30 ] 5 CMK-5-SO3H 20 130 S.F.…”

Green Route for Efficient Synthesis of Biologically Active Schiff Base Ligand Derived From 2 – Hydroxy Acetophenone: Structural, Spectroscopic, Anti Microbial and Molecular Modeling Studies

“…Green Chemistry approach is an eco-friendly approach and has tremendous applications for the synthesis of various organic compounds and key intermediates in recent past. This technique involves an alternative reaction media to replace hazardous and expensive solvents routinely used in organic synthesis 1 . Solvent free reactions need shorter reaction time, simpler and more efficient workup procedures, more improved selectivity's and easier separations and purifications than conventional solvents 2 .…”

A facile synthesis and antioxidant evaluation of conjugated 8‐azacoumarins based on DFT parameters

“…[6][7][8] Green chemical procedure is excessively utilized for the time being and became important in combinatorial chemistry. [12][13][14][15][16][17][18][19][20] The predominant mechanisms are suggested to illustrate the preventive function for antioxidant agents; the first one is the shift of H-atom, and the second one is a one-electron transmit mechanism. Flavonoids are still one of the major naturally occurring antioxidants, more over their presence in green leaves, fruits, olive, purple grapes, dark chocolate, and green tea.…”

“…[9][10][11] They possess interesting biological applications especially as antioxidant agents. [12][13][14][15][16][17][18][19][20] The predominant mechanisms are suggested to illustrate the preventive function for antioxidant agents; the first one is the shift of H-atom, and the second one is a one-electron transmit mechanism. The radicals emerging from both reactions (ArO • and ArOH •+ ) should be settled to stop the chain reactions [21][22][23][24][25] or as active center of flavonoid free radical scavenging.…”