- A NEW REACTION OF ACETYLENES, THE ADDITION OF METHANOL TO 5-HYDROXYHEX-3-YN-2-ONE. SYNTHESIS OF THE "ONION FURANONE", 2-HEXYL-5-METHYL-3-FURANONE.
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The conversion of alkyl-substituted 4-hydroxybut-2-ynones to 2,5-dialkyl-3-furanones via 2,5-dialkyl-methoxyfurans is described.
- Thomas, Alan F.,Damm, Hanne
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- An Unusual Substitution Reaction in a Benzotetrazine Derivative
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1-Methyl-3H-pyrazolobenzotetrazin-3-one decomposes in alcohols, with loss of nitrogen and intramolecular hydrogen transfer, to form 5-alkoxymethyl-1,2-dihydro-1-phenyl-3H-pyrazol-3-ones.
- Almerico, A. M.,Boulton, A. J.
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- Further enolate alkylation studies of 2,5-dimethyl-3(2H)-furanone
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Heterocyclic ketones, such as 2,5-dimethyl-3(2H)-furanone, provide multifunctional intermediates to various compounds. One property of these that has proven useful is the ability to alkylate the γ′-position of the dienolate. This report demonstrates the versatility of γ′-dienolate substitutions as employed toward syntheses of certain natural products and highly reactive electrophiles provide the best substrates for efficient substitution.
- Caine, Drury S.,Arant, Mark E.
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p. 2081 - 2086
(2007/10/03)
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- New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity
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A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety.
- Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara,Dall'Acqua, Francesco,Viola, Giampietro
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p. 5215 - 5223
(2007/10/03)
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- New Syntheses of Geiparvarin and 2,5-Dimethyl-3(2H)-furanone via CO2 Mediated Bond Reorganization
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A new synthesis of 3(2H)-furanones from 4-hydroxy-2-alkyn-1-one derivatives via CO2 mediated bond reorganization has been developed to the preparation of an antitumor agent, geiparvarin and a constituent of flavors, 2,5-dimethyl-3(2H)-furanone.
- Inoue, Y.,Ohuchi, K.,Imaizumi, S.,Hagiwara, H.,Uda, H.
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p. 3063 - 3068
(2007/10/02)
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- Silyl Nitronates in Organic Synthesis. Routes to Heterocycles and Cyclopentanoids. Synthesis of Allethrolone and Calythrone. Acylation and Cyanohydroxylation of Double Bonds. An Exploratory Study
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Silyl nitronates are versatile reagents for the preparation of heterocycles by dipolar addition to double bonds.The intermediate isoxazolidines can be transformed to 2-isoxazolines, isoxazoles, furans, dihydrofuranones, pyrazoles, pyridazines and pyridazones.Reduction of 2-isoxazolines with Ti3+ leads to hydroxylated 1,4-diketones, which subsequently can be cyclized to cyclopentenones.Routes to calythrone, rethrolones, prostanoids and a number of naturally occurring dihydrofuranones are devised, as well as synthetic procedures for acylation, preparation of endiones, hydroxyacylation, cyanation and hydroxycyanation of double bonds.
- Andersen, Soeren H.,Das, Nalin B.,Joergensen, Ruth D.,Kjeldsen, Gunhild,Knudsen, Jes S.,et al.
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- Process for preparing 2,5-dimethyl-3-(2H)-furanone
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There is disclosed a simple, economical process for preparing 2,5-dimethyl-3-(2H)-furanone by hydrolysis of the dimer of diacetyl at a temperature of 20°C to 120°C and in the presence of an acid, mineral or organic, or of a cationic resin, with elimination of a acetic acid.
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