Different types of 3-substituted 4H-4-oxobenzopyrans were prepared by microwave irradiation as well as by a classical method. The beneficial effect of microwave irradiation on the aldol condensation of 3-formylchromones with 2-imino-1-methylimidazolidine-4-one (creatinine), 2-thioxoimidazolidine-4-one (thiohydantoin) and 2-ethyl-2-thioxothiazolidin-4-one (3-ethylrhodanine) in different reaction media is described. Our results show that the effect of microwave irradiation on the reactions studied was a shortening of the reaction times and a smooth increase in the yields. The subsequent reactions of the product with some nucleophiles are discussed. The structure of the products was proven by elemental analysis, IR and NMR spectra.
Condensation of 6-R-3-formylchromones (I) with 3,3-dimethyl-1,3-cyclohexanedione (II), 1,3-indandione (III), 1,2e-biindenylidene-3,1e,3e-trione (bindone, IV), 2-oxo-1,4-benzothiazine (V) and 3-oxo-2,3-dihydro-1-thia-3a,8-diazacyclopent[a]indene (VI) by the "classical" method, as well as condensation in a microwave oven, has been studied. Some subsequent reactions of these products are described.
This review presents a survey of the condensations of 3-formylchromone with various active methylene and methyl compounds, e.g. malonic or barbituric acid derivatives, five-membered heterocycles, etc. The utilisation of the condensation products for the synthesis of different heterocyclic systems, which is based on the ability of the γ-pyrone ring to be opened by the nucleophilic attack is also reviewed. Finally, the applications of microwave irradiation as an unconventional method of reaction activation in the synthesis of condensation products is described and the biological activity of some chromone derivatives is noted.
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