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- W2888943885 abstract "P yrone derivatives represent an important class of naturally occurring lactones, which are structural subunits in numerous natural products that exhibit a wide range of biological activities, such as antimicrobial, androgen-like, phytotoxic, antifungal, and pheromonal effects. A simple, convenient and efficient procedure was proposed for the synthesis of 3-arylpyran-2-one-6-carboxylic acids from the reaction of appropriate pyran-2-ones and arenediazonium chlorides under Meerwein reaction conditions. Starting 2-oxo-2 H -pyran-6-carboxylic acid were synthesized by interaction of trichloroacetyl chloride and (2 E )-but-2-enoyl chloride with triethylamine in a dichloromethane as a solvent, with further heating of the product – 6-(trichloromethyl)-2 H -pyran-2-one to 80 o C in the medium of sulfate acid. It was found that this substrate was arylated selectively into 3-position of pyran-2-one. In this way we obtained derivatives of such compounds: 3-(4-nitrophenyl)-2-oxo-2 H -pyran-6-carboxylic acid, 3-(3,4-dichlorophenyl)-2-oxo-2 H -pyran-6-carboxylic acid, 3-(4-chlorophenyl)-2-oxo-2 H -pyran-6-carboxylic acid, 3-(4-acetylphenyl)-2-oxo-2 H -pyran-6-carboxylic acid and 3-(4-bromophenyl)-2-oxo-2 H -pyran-6-carboxylic acid. This method of obtaining substituted 3-aryl-2-oxo-2 H -pyran-6-carboxylic acids is general utility compared to other methods and it is a good alternative to transition-metal-catalyzed arylation reactions because it is ligand free and uses inexpensive and commercially available reagents and catalysts. The structures of products have been confirmed by 1 H, 13 C NMR spectra and single crystal X-ray data analysis for 3-(4-bromophenyl)-2-oxo-2 H -pyran-6-carboxylic acid. Meerwein reaction products – the 3-aryl-2-oxo-2 H -pyran-6-carboxylic acids are convenient scaffolds for further organic synthesis. Keywords : arylation , 2- pyrone -6-carboxylic acid , Meerwein reaction, arenediazonium salts . P yrone derivatives represent an important class of naturally occurring lactones, which are structural subunits in numerous natural products that exhibit a wide range of biological activities, such as antimicrobial, androgen-like, phytotoxic, antifungal, and pheromonal effects. A simple, convenient and efficient procedure was proposed for the synthesis of 3-arylpyran-2-one-6-carboxylic acids from the reaction of appropriate pyran-2-ones and arenediazonium chlorides under Meerwein reaction conditions. Starting 2-oxo-2 H -pyran-6-carboxylic acid were synthesized b y interaction of trichloroacetyl chloride and (2 E )-but-2-enoyl chloride with triethylamine in a dichloromethane as a solvent, with further heating of the product – 6-(trichloromethyl)-2 H -pyran-2-one to 80 o C in the medium of sulfate acid. It was found that this substrate was arylated selectively into 3-position of pyran-2-one. In this way we obtained derivatives of such compounds: 3-(4-nitrophenyl)-2-oxo-2 H -pyran-6-carboxylic acid, 3-(3,4-dichlorophenyl)-2-oxo-2 H -pyran-6-carboxylic acid, 3-(4-chlorophenyl)-2-oxo-2 H -pyran-6-carboxylic acid, 3-(4-acetylphenyl)-2-oxo-2 H -pyran-6-carboxylic acid and 3-(4-bromophenyl)-2-oxo-2 H -pyran-6-carboxylic acid. This method of obtaining substituted 3-aryl-2-oxo-2 H -pyran-6-carboxylic acids is general utility compared to other methods and it is a good alternative to transition-metal-catalyzed arylation reactions because it is ligand free and uses inexpensive and commercially available reagents and catalysts. The structures of products have been confirmed by 1 H, 13 C NMR spectra and single crystal X-ray data analysis for 3-(4-bromophenyl)-2-oxo-2 H -pyran-6-carboxylic acid. Meerwein reaction products – the 3-aryl-2-oxo-2 H -pyran-6-carboxylic acids are convenient scaffolds for further organic synthesis. Keywords : arylation , 2- pyrone -6-carboxylic acid , Meerwein reaction, arenediazonium salts ." @default.
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- W2888943885 date "2018-01-01" @default.
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- W2888943885 title "Pyran-2-one-6-carboxylic acid under Meerwein reaction conditions" @default.
- W2888943885 doi "https://doi.org/10.30970/vch.5902.311" @default.
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