Abstract
Oxygen-containing heterocycles are largely distributed in natural and synthetic compounds. Coumarins are among the most famous heterocycles which possess one oxygen atom in their rings. Coumarins are classified as multifunctional scaffold and are used as anti-oxidant reagents, anti-inflammatory, anti-microbial, anti-fungal, anti-HIV active, analgesic, anti-histaminic, insecticides, dyes, herbicides, sensitizers, perfumes, cosmetics and food additives. Due to their diverse applications in industrial and pharmaceutical fields, many chemists have given significant interest to these compounds. Herein, the review highlights various methods for the synthesis and interactions of coumarin moiety as one of the most efficient categories of heterocycles.
Highlights
Coumarins have been known as fragrance materials in perfumes for a rather long time, because of their sweet smell
Coumarin derivatives have been used as antioxidant reagents,[3] dyes,[4] insecticides,[5] sensitizers,[6] herbicides, food additives, perfumes, and cosmetics (Fig. 1)
Coumarins are an important class of compounds of natural and synthetic origin
Summary
Coumarins have been known as fragrance materials in perfumes for a rather long time, because of their sweet smell. Friedel-Crafts condensation of substituted malonic acid derivative (5) with phenol (4) to produce various 3-substituted 4-hydroxycoumarin compounds.[19] In this study, a photoaffinity derivative of 4-hydroxycoumarin (8) was synthesized by the introduction of a p-azidobenzyl group at the 3-position through the condensation of p-nitrobenzylmalonic acid with phenol followed by reductive to give (7) The latter was converted to the azido compound (8) (Fig. 7).[21]. The cyclocondensation of (15a-c) with diethyl carbonate in dry toluene room temperature in the presence of potassium tert-butoxide, afforded the 4-hydroxycoumarins (16a-e) The treatment of these compounds with a large excess of piperazine at 160°C, good yields of the corresponding 4-(1-piperazinyl) coumarins (17a-e) were obtained (Fig. 11). 4-Hydroxycoumarins (37) was prepared by treatment of α-halocarboxylic acid esters of salicylaldehyde, ohydroxyacetophenone, and methyl salicylate (35), with sodium or lithium telluride (Fig. 16).[34]
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