- Scalable Synthesis of 3-Ethyl-4-methyl-1,5-dihydro-2 H -pyrrol-2-one: An Important Building Block of the Antidiabetic Drug Glimepiride
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A four-step, practical, and easily scalable synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one, an important building block of the antidiabetic drug glimepiride, has been accomplished. Key features are the synthesis of 3-methyl-4-hydroxy-2-butenolide in water and triflic acid mediated N-benzyl lactam N-deprotection. The main advantages of this process are the scalable synthetic route and decreased number of reaction steps, which paves the way for the industrial-scale synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one.
- Chavan, Subhash P.,Pawar, Ambaji A.,Patil, Niteen B.,Kadam, Appasaheb L.,Shinde, Shrikrishna S.
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- Synthesis of a 13C-labelled seed-germination inhibitor (3,4,5-trimethylfuran-2(5H)-one) for the mode of action elucidation
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Abstract: It has been found that the butenolide 3,4,5-trimethylfuran-2(5H)-one, isolated from plant-derived smoke, efficiently inhibits seed germination and significantly reduces the effect of the highly active germination promotor karrikinolide (KAR
- Po?ta, Martin,Soós, Vilmos,Beier, Petr
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- THREE COMPONENT CO-CRYSTAL FORMATION BETWEEN DIASTEREOMERIC MIXTURES OF 3-ALKYL-4-((S)-1'PHENYLETHYLAMINO) BUTANOIC ACID AND OPTICALLY PURE 1, 1'-BI-2-NAPHTHOL
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A ternary co-crystal consisting of 1 :0.5:0.5 molar proportion of (S)-1,1'-bi-2-naphthol, 3(S)-propyl-4-[(S)1 '-phenyl-ethylamino]-butanoic acid and 3(R)-propyl-4-[(S)1'- phenyl-ethylamino]-butanoic acid having characteristic powder X-ray diffraction pattern with 2Θ values of 8.41, 9.38, 10.32, 12.16, 15.52, 15.51, 17.84, 17.95, 19.16, 20.37, 21.74, 22.55, 24.44, 25.65, 28.40, 29.15, 29.69, 31.31, 33.54, 34.40, 35.43 (±0.2) and having differential scanning calorimetric peak at about 189.23 ° C when analyzed at the rate of heating of 10°C per minute and process for preparing the same. A process for resolution of (S)-1,1'-bi-2-naphthol from RS-1,1'-bi-2-naphthol.
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Page/Page column 21-22
(2012/02/02)
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- Synthesis of γ-hydroxybutenolides applying crossed aldol condensation in the presence of a bulky Lewis acid and their anti-tumor activity
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An improved synthesis of γ-hydroxybutenolides 1a - d was achieved via crossed aldol condensation between aldehydes 2a - d and the protected γ-hydroxy-β-methylbutenolides 3 or 4 using the bulky Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH). Using this same methodology, the γ-hydroxybutenolides 17a - d having various heteroaromatic rings were synthesized and their anti-tumor activities were evaluated.
- Yamano, Yumiko,Fujita, Yumi,Mizuguchi, Yukari,Nakagawa, Kimie,Okano, Toshio,Ito, Masayoshi,Wada, Akimori
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p. 1365 - 1370
(2008/09/16)
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- A mild, efficient and general method for the synthesis of trialkylsilyl (Z)-4-oxo-2-alkenoates and γ-hydroxybutenolides
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2-Trialkylsilyloxyfurans react rapidly with dimethyldioxirane at -78°C to provide trialkylsilyl (Z)-4-oxo-2-alkenoates whose hydrolysis delivers γ-hydroxybutenolides with high efficiency; a short synthesis of a naturally occurring monoterpene γ-hydroxybutenolide (4) is reported.
- Boukouvalas, John,Lachance, Nicolas
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- 4-ARYL- AND 4-ARYLTHIO-5-HYDROXY-2(5H)-FURANONES AS INHIBITORS OF PHOSPHOLIPASE A2
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The invention provides novel 5-hydroxy-4-aryl- and 5-hy-droxy-4-(arylthio)-2(5H)-furanones of the following structure: wherein R contains from about five to about twenty carbon atoms and is defined herein; X is oxygen, sulfur, S02, NH, N(lower alkyl), N(lower acyl), aminocarbonyl, carbonyl, carbonylamino, CH2 or a carbon-carbon bond; Y is hydrogen, halogen, lower alkyl, nitro, alkylthio, perfluoroalkyl, hydroxy, or lower alkoxy(C1-C8); Z is sulfur or a carbon-carbon bond; and Q is H, an alkyl of from 1-20 carbon atoms, COR', COOR', CONHR', PO(OR')2, PO(OR')R" wherein R' and R" are independently selected from the group consisting of H, an alkyl of from 1-20 carbon atoms, phenyl, and substituted phenyl and prodrugs thereof and pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprising these compounds, methods of using these compounds as inhibitors of inflammation and for treating other diseases characterized by the overproduction of arachidonic acid metabolites, intermediates and methods of preparing these compounds are also provided.
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- The Preparation of Synthetic Analogues of Strigol
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A range of analogues of the natural germination stimulant, strigol, for parasitic weeds of the genera Striga and Orobanche, has been prepared.Most of the products contain an α-formyl-γ-lactone (or α-formyl-γ-lactam) grouping attached through an enol-ether linkage to the 5-position of a but-2-enolide.Some have shown sufficiently high activities as to warrant large-scale field trials.
- Johnson, Alan W.,Gowda, Gopala,Hassanali, Ahmed,Knox, John,Monaco, Sam,et al.
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p. 1734 - 1743
(2007/10/02)
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- Lactone Chemistry. Synthesis of β-Substituted, γ-Functionalized Butanolides and Butenolides and Succinaldehydic Acids from Glyoxylic Acid
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The Mannich-type aminoalkylation reaction of enolizable aldehydes with morpholine and glyoxylic acid instead of formaldehyde was investigated: in basic and neutral media were obtained α,γ-dimorpholinobutanolides 2 and α-morpholino-γ-hydroxybutanolides 1, respectively.In acidic medium the spontaneous elimination of the α-morpholino group afforded the γ-hydroxybutenolide 8.The reaction pathways were suggested from the isolation and characterization of some intermediates of the Mannich reaction.These lactone structures constitute versatile synthetic intermediates for the preparation of β-substituted succinaldehydic acids 15 and 5-substituted 3-(2H)-pyridazinones 13 and 14.
- Bourguignon, J. J.,Wermuth, C. G.
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p. 4889 - 4894
(2007/10/02)
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