Overview on developed synthesis procedures of coumarin heterocycles
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REVIEW
Overview on developed synthesis procedures of coumarin heterocycles Masoud Mohammadi Zeydi1 · Seyed Jafar Kalantarian1 · Zahra Kazeminejad1 Received: 12 April 2020 / Accepted: 18 June 2020 © The Author(s) 2020
Abstract Considering highly valuable biological and pharmaceutical properties of coumarins, the synthesis of these heterocycles has been considered for many organic and pharmaceutical chemists. This review includes the recent research in synthesis methods of coumarin systems, investigating their biological properties and describing the literature reports for the period of 2016 to the middle of 2020. In this review, we have classified the contents based on co-groups of coumarin ring. These reported methods are carried out in the classical and non-classical conditions particularly under green condition such as using green solvent, catalyst and other procedures. Keywords Coumarins · Biological · Pharmaceutical · Heterocycles
Introduction Coumarins or benzopyran-2-ones are a group of natureoccurring lactones first derived from Tonka beans in 1820. Those compounds are valuable kinds of oxygen containing heterocycles widely found in nature, so that they have been routinely employed as herbal medicines since early ages. More than 1300 coumarin derivatives have been identified, which are mainly obtained from the secondary metabolite in green plants, fungi and bacteria [1]. This led to an incentive for researchers around the world to investigate the nature and identification of this molecule. Since the reporting of the first synthetic route in 1882, this moiety has found its place in fabric conditioners, certain perfumes and in medicinal industry especially as anti-coagulants, viz. warfarin and dicoumarol; also some others such as naturally occurring coumarins moieties have been reported (Fig. 1). Also, many synthetic coumarins with a type of pharmacophoric groups at C-3, C-4 and C-7 positions have been intensively screened for different biological properties. In recent years, there has been considerable amount of researches with coumarins being tested for anti-HIV [2, 3], anticancer [4–8], anti-microbial [9, 10], anti-tumor [6, 11], antioxidant [12, * Masoud Mohammadi Zeydi [email protected] 1
Department of Chemistry, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran
13], anti-Alzheimer [14], anti-tuberculosis [15], anti-platelet activity [16], COX inhibitors [17], anti-inflammatory [18], anti-asthmatic [19], anti-viral [20] and DNA gyrase inhibitors [21].
Discussion Coumarins containing triazole core An efficient method was reported by Awasthi et al. for the synthesis of coumarin–triazole derivatives 7 via the alkylation reaction of 7-hydroxy-4-methyl coumarin 3 with propargyl bromide 4 in dry acetone and anhydrous potassium carbonate at 50 °C and then reaction with various sodium azides 6 (Scheme 1). Most of the synthesized compounds 7 exhibited anti-plasmodial activity against chloroquinesensitive strain of plasmodium falciparum [22]. 7-Alkynyl-substituted coumarins 9 were prepared by a
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