Abstract
The approach to 3-(furan-2-yl)-1,3-di(het)arylprop-2-en-1-ones based on the oxidative dearomatization of 3-(furan-2-yl)-1,3-di(het)arylpropan-1-ones followed by an unusual cyclization of the formed di(het)aryl-substituted 2-ene-1,4,7-triones has been developed. The cyclization step is related to the Paal–Knorr synthesis, but the furan ring formation is accompanied in this case by a formal shift of the double bond through the formation of a fully conjugated 4,7-hydroxy-2,4,6-trien-1-one system or its surrogate.
Highlights
We found that the oxidation of substrates followed by treatment compounds using Michael addition of 2-substituted furans to α,β-unsaturated carbonyl by treatment withIndeed, trifluoroacetic (TFA)
We started this study by searching for optimal reaction conditions for oxidation of model furan 1a
THF leads to the formation of (E)-2a with 77% yield while application of m-chloroperbenzoic acid (m-CPBA) afforded (Z)-2a [33] as the exclusive product in 87%
Summary
Furosemide is a potent loop diuretic that is used for edema secondary to congestive heart failure exacerbation, liver and kidney failure, and high blood pressure [14,15] Due to their versatile reactivity, furans are intensively used in organic synthesis as universal building blocks for the preparation of various useful products, including natural compounds [16,17,18,19,20]. Molecules 2021, 26, 2637 the formation of a key spiro-intermediate B, the hydrolysis of which results in the formation of functionalized furans in moderateB, to the good yields.
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