Abstract
3,3-(Butane-1,4-diyl)bis(1,2-dimethyl-1 H -imidazole-3-ium)bromide ([BDBDMIm]Br) is easily used as an efficient and recyclable ionic liquid for the synthesis of bis coumarinyl methanes in the presence of a catalytic amount of ceric ammonium nitrate (CAN) under grinding. All reactions are performed in the absence of solvent in excellent yield during short reaction time. Furthermore, the ionic liquid can be reused and recovered for several times without loss of activity. This method provides several advantages such as simple work-up, environmental friendliness and shorter reaction time along with high yields. All of synthesized compounds were characterized by infrared spectroscopy, 1 H and 13 C nuclear magnetic resonance spectroscopy and elemental analyses. KEY WORDS : Grinding, Ionic liquid, CAN, 4-Hydroxycoumarin, Oxidation, One-pot Bull. Chem. Soc. Ethiop. 2017 , 31(2), 323-329. DOI: http://dx.doi.org/10.4314/bcse.v31i2.13
Highlights
Coumarin constitutes one of the major classes of naturally occurring compounds
Looking for the eco-friendly alternatives to synthesize of bis coumarinylmethanes at mild and practical protocols, we report the synthesis of bis coumarinylmethanes using [BDBDMIm]Br-ceric ammonium nitrate (CAN) under grinding as a green and novel method (Scheme 1)
As part of our interest for the development of efficient and environmentally friendly procedures for the synthesis of heterocyclic and pharmaceutical compounds [13,14,15,16], an efficient, facile and solvent free procedure was introduced for the synthesis of bis coumarinylmethane through the reaction of one equivalent of synthesized aldehyde and two equivalent of 4-hydroxycoumarin in the presence of ionic liquid [BDBDMIm]Br
Summary
Coumarin constitutes one of the major classes of naturally occurring compounds. In the wellknown family of coumarin derivatives, dimeric coumarins ( called biscoumarins) occupy an interesting position. Some types of these compounds could be isolated from plants [1], we are interested in its chemistry because of its benefits as biologically active agents. It represents the core structure of several molecules of pharmaceutical importance. Coumarin has been reported to serve as anti-cancer [2], anti-microbial [3], anti-inflammatory [4] and anticoagulant [5]. These pharmacological properties of coumarin encouraged us to synthesize some coumarin derivatives. Looking for the eco-friendly alternatives to synthesize of bis coumarinylmethanes at mild and practical protocols, we report the synthesis of bis coumarinylmethanes using [BDBDMIm]Br-CAN under grinding as a green and novel method (Scheme 1)
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