Synthesis, Characterization, and Optimization of Novel Furan-ring Fused Chalcones via Radical Cyclization of α,β-Unsaturated Ketones and Cyclic Ketone

Abstract

: Novel Furan-ring Fused Chalcones (FFC) were synthesized using a radical cyclization reaction of α,β-unsaturated ketones with cyclic ketone as the model reaction to attain this goal. In this study, traditional and microwave-assisted methods for the efficient and cost-effective synthesis of furan-ring fused chalcones in mild reaction conditions are compared and optimized. The goal is to develop a reliable and adaptable synthetic technique that may be used to produce these useful chalcone derivatives quickly and effectively. The optimal experimental conditions for these reactions were carefully determined using two independent methodologies: conventional (Method A) and microwave (Method B). The results indicated that the proposed method B could be used effectively in the future to synthesize novel furans with short reaction times and acceptable yields (87-94 %), and products were purified by column chromatography and preparative thin layer chromatography (PTLC). All new compounds were characterized by 1H-NMR, 13C-NMR, LC-MS, and elemental analyses. result: The aim of this work was to synthesize a new series of furan-ring fused chalcones using two methods and to show the advantages of microwave when it is compared to conventional synthesis methods. As shown in Table 2, a series of novel compounds (3a-3e) were synthesized in one-step reaction between α,β-unsaturated ketones (1a, 1b), and active methylene compounds (2a-d) (Figure 1). The structures of these compounds were confirmed by several spectroscopic methods (1H NMR, 13C NMR, mass spectra, and elemental analysis). conclusion: We have developed a novel, highly efficient, catalyst-free, green protocol for the one-pot three-component synthesis of furan-ring fused chalcones derivatives. This protocol has the advantages of mild reaction conditions, high yields, convenient operation, and environmental friendliness. The technique has various benefits, most notably a decrease in reaction time, good to high yields, and purer results. This work used microwave irradiation, which reduced the reaction time and produced higher yields than the traditional techniques