- Rhodium(II) Acetate-Catalyzed Reaction of 2-Amino-4,5-dihydro-3-furancarbonitriles with Dialkyl Diazomalonates
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2-Amino-4,5-dihydro-3-furancarbonitriles 3 react with dialkyl diazomalonates in the presence of rhodium(II) acetate to yield dialkyl (5-amino-4-cyano-2,3-dihydro-3-furanyl)propanedioates 4. Dehydrogenation of 4 with DDQ provided dialkyl (5-amino-4-cyano-3
- Yamagata, Kenji,Okabe, Fumi,Yamazaki, Motoyoshi
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- Highly diastereoselective thermal decomposition of 3-(azidomethylene)dihydrofuran-2-one
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Thermal decomposition of 3-(azidomethylene)dihydrofuran-2-one in various solvents at temperatures above 70°C gave a spiroaziridine derivative with an excellent diastereoselectivity. A mechanism of this new kind of substituted vinyl azide decomposition has been suggested based mainly on the stereochemistry and kinetic data of the reaction. A spiroazirine derivative proposed as a reaction intermediate was trapped by the decomposition of title azide in acetic anhydride.
- Mazal, Ctibor,Jonas, Jaroslav,?ák, Zdirad
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- Preparation method of 3-aminomethyl tetrahydrofuran
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The invention relates to a preparation method of 3-aminomethyl tetrahydrofuran. Specifically the invention relates to a method of preparing 3-aminomethyl tetrahydrofuran through reducing 3-cyano-gamma-butyrolactone. A novel synthesis technology is adopted. Ethyl cyanoacetate and ethylene oxide carry out cyclization reactions under an alkaline condition to obtain 3-cyano-gamma-butyrolactone; then 3-cyano-gamma-butyrolactone is reduced to obtain 2-aminomethyl-1,4-butylene glycol, and finally 2-aminomethyl-1,4-butylene glycol carries out dehydration and cyclization reactions to obtain 3-aminomethyl tetrahydrofuran. The synthesis technology has the advantages of easily available raw materials, simple operation, mild reaction conditions, high yield and product purity, little environmental pollution, and low production cost, is suitable for industrial massive production, and has a wide application prospect.
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Paragraph 0022; 0023; 0024; 0025; 0026; 0036-0039; 0046-0049
(2017/08/29)
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- Manganese(III) γ-Lactone Annulation with Substituted Acids
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Manganese(III) acetate oxidation of several HOOCCH2X, X = electron withdrawing group, in the presence of alkenes led to the formation of α-substituted γ-lactones.Chloroacetic acid gave α-chloro-γ-lactones, which were converted in two steps to the corresponding α,β-unsaturated γ-lactones. 3-Chloropropanoic acid led to the α-methylene γ-lactone after base induced elimination of HCl.Cyanoacetic acid produced α-cyano γ-lactones which could be hydrolytically decyanated or converted to the α-methylene γ-lactones in two steps.Potassium methyl malonate was oxidized and annulated onto alkenes to give α-carbomethoxy γ-lactones in reasonable yields.The method demonstrates a general route into several useful types substituted γ-lactones.
- Fristad, William E.,Peterson, John R.,Ernst, Andreas B.
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p. 3143 - 3148
(2007/10/02)
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