Green synthesis of bis‐coumarin derivatives using Fe(SD)₃as a catalyst and investigation of their biological activities

Abstract

A convenient, practical, green, and environmentally friendly method was developed for the synthesis of biscoumarins and corresponding tetrakis products from the reaction of 4-hydroxycoumarin and various aldehydes. The bis-coumarins were synthesized in high yield under mild reaction conditions. Products were obtained in the presence of in situ prepared Fe(SD) 3 [Iron(III) dodecyl sulfate] as a combined Lewis acid-surfactant catalyst (LASC) in water in short reaction times. Also, the antibacterial activity of compounds was screened against Pseudomonas aeruginosa and Escherichia coli as Gram-negative bacteria and Micrococcus luteus and Staphylococcus aureus as Gram-positive bacterial strains. Products 3g, 3k-l were most active than cefotaxime against E. coli and also compounds 3c and 3g were most active than cefotaxime against S. aureus.

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

“…Acetamide or guanidine remained unchanged and was recovered after the reaction. For this reaction, Mahmoodi and co-workers [79] have presented a user-friendly and rational scheme to develop biscoumarins from aldehydes and 4HC in aqueous medium using in situ iron (III) dodecyl sulphate [Fe(SD) 3 ] as a united acid-surfactant catalyst at 100°C temperature (Scheme 8 : Method 2). The catalyst Fe(SD) 3 was formed in reaction from FeCl 3 .6H 2 O and sodium dodecyl sulphate.…”

Efficient one-pot synthesis of 4-hydroxy-2H chromene by heterogeneously catalyzed ZnO NP and mesoporous aluminosilicate catalysts in solvent free condition

“…Till date, available procedure of chromene derivatives includes Pechmann, Reformatsky, Perkin, Knoevenagel, and wittig reaction. Among these, the knoevenagel condensation route is most preferred method [42] , in which generally acid catalyst such as OBS,SDS,TBAB, Sulphonated catalyst, fluoride, chloride etc was employed [36][37][38][39][40][41][42][43] .…”

Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

“…Knoevenagel-Michael addition reaction is highly significant in organic chemistry for the formation of C-C bonds and most commonly used for the synthesis of biscoumarins and bisdimedones. In this context, many practical procedures using several catalysts such as HAP/Fe 3 O 4 NPs [41], lipase RMIM enzyme [42], Fe 3 O 4 @ SiO 2 -silylcyclopropyldimethylglyoxime-Ni superparamagnetic NPs [43], Fe 3 O 4 @ SiO 2 @Ni-Zn-Fe LDH [44], Bi(NO 3 ) [46], P4VPy [47], Fe(SD) 3 [48], taurine [49], HY zeolite [50], CuFe 2 O 4 @SiO 2 @PTMS@ Tu@Ni(II) [51] and Fe 3 O 4 @sulfosalicylic acid MNPs [52] have been reported by the researchers for the synthesis of biscoumarins. Moreover, bisdimedone derivatives have been synthesized using several catalysts, viz.…”