Overview on developed synthesis procedures of coumarin heterocycles

Masoud Mohammadi Zeydi,Zahra Kazeminejad,Seyed Jafar Kalantarian

doi:10.1007/s13738-020-01984-1

Masoud Mohammadi Zeydi, Zahra Kazeminejad + Show 1 more

Open Access

https://doi.org/10.1007/s13738-020-01984-1

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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.

Highlights

Coumarins or benzopyran-2-ones are a group of natureoccurring lactones first derived from Tonka beans in 1820
Complete hydrolysis of 1,3-oxazines/ coumarins led to N-acylmalonamic acids 19, and the reaction of 1,3-oxazines/coumarins with hydrazines or phenylhydrazine in glacial acetic acid led to coumarins containing 1,2,4-triazole derivatives (Scheme 3) [24]
The reaction of epichlorohydrin with 7-hydroxy-4-methyl-2H-chromen-2-one 3 under reflux conditions yielded 4-methyl-7-(oxiran-2-ylmethoxy)2H-chromen-2-one 22 and reaction of 22 with various azoles led to a series of coumarin-derived azolyl ethanols including imidazolyl 23, triazolyl 24, tetrazolyl 25, benzotriazolyl 26, thiol-imidazolyl and thiol-triazolyl ones (Scheme 4)

Summary

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. 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

Conclusions

Compliance with ethical standards