FUNCTIONALIZATION OF COUMARIN DERIVATIVES BASED ON 3-(5-HYDROXYBENZOFURAN-3-CARBONYL)-2H-CHROMEN-2-ONE
DOI: https://doi.org/10.17721/1728-2209.2024.1(59).8
Keywords:
coumarin, alkylation, heterocyclization, amidoxime, 3-(5-hydroxybenzofuran-3-carbonyl)-2H-chromen-2-oneAbstract
Background. Coumarins (benzopyran-2-ones) and benzofurans belong to an important class of natural compounds and have long attracted significant scientific attention due to their diverse biological properties and high synthetic potential for structural modification. Introducing functional groups and pharmacophoric substituents into the structure of coumarins with a benzofuran fragment is a relevant and practically oriented task. The aim of the presented study was to explore the possibilities of structural modification of 3-(5-hydroxybenzofuran-3-carbonyl)-2H-chromen-2-one and to introduce additional functional groups into its structure, such as amino groups, hydroxyl groups, amidoxime fragments, and oxadiazole rings – key moieties for the creation of new pharmaceuticals, agrochemicals, and functional materials. The objects of study include alkylation, amidation, heterocyclization, and epoxide ring-opening as approaches to create structurally diverse derivatives based on 3-(5-hydroxybenzofuran-3-carbonyl)coumarin, along with the spectral characteristics of the synthesized compounds.
Methods. Organic synthesis of new functionalized derivatives based on 3-(5-hydroxybenzofuran-3-carbonyl)coumarin; structure elucidation and characterization of the synthesized compounds using 1H and 13C NMR spectroscopy.
Results. Using 3-(5-hydroxybenzofuran-3-carbonyl)-2H-chromen-2-one as a model compound allowed for its structural modification
and demonstrated its utility as a reagent for introducing additional functional groups such as amino groups, hydroxyl groups, amidoxime fragments, and oxadiazole rings. By employing reactions like alkylation, amidation, and heterocyclization, preparative methods for synthesizing a series of functionalized derivatives were developed, including 2-((3-(2-oxo-2H-chromen-3-carbonyl)-benzofuran-5-yl)oxy)acetonitrile, 3-(5-(oxiran-2-yl-methoxy)-benzofuran-3-carbonyl)-2H-chromen-2-one, N'-hydroxy-2-((3-(2-oxo-2H-chromen-3-carbonyl)benzofuran-5-yl)oxy)-acetimidamide,
3-(5-((1,2,4-oxadiazol-3-yl)methoxy)benzofuran-3-carbonyl)-2H-chromen-2-one, and hydroxy-3-(alkylamino)propoxy)-benzofuran-3-carbonyl)coumarins with high yields.
Conclusions. The study demonstrated that 3-(5-hydroxybenzofuran-3-carbonyl)coumarin can be effectively used as a convenient starting reagent for the synthesis of structurally diverse coumarin derivatives, particularly those with amino groups, hydroxyl groups, amidoxime fragments, and oxadiazole rings. The efficiency and convenience of the developed synthetic procedures allow for the production of target products with high yields and in multi-gram quantities.
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