- The Convenient Synthesis of 11-Methyl-3,8-disubstituted-12-aryl-3,4,7,8,9,12-hexahydro-1H-chromeno[2,3-b]quinoline-1,10(2H)-dione Derivatives
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The 2-arylidene-3-oxobutanenitrile derivatives 2 were prepared by the Knoevenagel condensation between aldehydes and 3-oxobutanenitrile 1, which was obtained by acid hydrolysis of β-aminocrotononitrile. 3-Acetyl-2-amino-4H-chromen-5(6H)-one derivatives 3 were synthesized by reaction of 2-arylidene-3-oxobutanenitrile 2 and 5-substituted-1,3-cyclohexanedione in ethylene glycol. The 11-methyl-3,8-disubstituted-12-aryl-3,4,7,8,9,12-hexahydro-1H-chromeno[2,3-b]quinoline-1,10(2H)-dione derivatives 4 were obtained by Friedl?nder reaction of compounds 3 with 5-substituted-1,3-cyclohexanedione, using p-toluenesulfonic acid monohydrate as catalyst. The structures of all novel compounds were characterized by elemental analysis, IR, MS, and 1H NMR spectra. The crystal and molecular structure of compound 4f has been determined by single crystal XRD analysis.
- Han, Guang-Fan,Zhao, Li-Jun,Chen, Li-Zhuang,Du, Jia-Wei,Wang, Zhong-Xia
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- Magnesium Halide-Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes
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MgX2-catalyzed annulation of methylenecyclopropanes with acyl cyanoalkenes was accomplished to give oxaspiro[2.5]octenes in excellent yields. The reaction proceeded through a rare intramolecular oxa-Michael addition of Mg enolate. The oxaspiro
- Ogura, Kazuki,Shibata, Ikuya,Shimazu, Jun-ya,Suzuki, Itaru
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supporting information
p. 2785 - 2787
(2021/06/26)
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- HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
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Page/Page column 75
(2012/11/08)
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- Aryl halides as precursors of electrogenerated bases. Utilization in coupling reactions of acetonitrile with various electrophilic compounds
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An electrochemical alternative to classical cyanomethylation is possible by using electrogenerated bases (EGBs), obtained by electroreduction of aryl halides in an undivided cell fitted with a cadmium coated cathode and a sacrificial magnesium anode. Acetonitrile is used both as solvent and as hydrogen-active compound. A coupling reaction with various electrophilic compounds was carried out. When the electrophilic compound was present from the beginning of the electrolysis, the expected coupling product with the cyanomethyl anion was obtained. If the electrophilic compound was added only after complete electrolysis of the aryl halide, dimerization of the cyanomethyl anion and a coupling reaction between the dimer anion and the electrophilic compound were observed.
- Barhdadi, Rachid,Gal, Jacques,Heintz, Monique,Troupel, Michel,Perichon, Jacques
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p. 5091 - 5098
(2007/10/02)
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- ON THE RING CLEAVAGE OF ISOXAZOLES: A NOTE
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A new heterocyclic compound is obtained from the basic cleavage of an isoxazole ring in the presence of an aldehyde.
- Ciller, Juan Antonio,Seoane, Carlos,Soto, Jose Luis
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p. 1989 - 1993
(2007/10/02)
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- Ring Cleavage Reactions of 3- and 5-Non-substituted Isoxazoles
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5-Methylisoxazoles with electron-accepting groups at C-4 (Ia-c) and 2,3-dimethylisoxazolium iodide (II) undergo ring cleavage when treated with organic bases.The nature of the open chain products which were obtained (stable enolates, β-diketones, esters) depends on the group at C-4 and the strength of the base.In some of these processes aromatic aldehydes were used in order to determine the competition between the condensation and the cleavage reaction.The mechanism of the nucleophilic ring cleavage of II is also shown.
- Alberola, A.,Gonzalez, A. M.,Guerra, D.,Pulido, F. J.
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p. 1073 - 1076
(2007/10/02)
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