- 4,6-Dimethylpyridine-2,3-dicarbonitrile and its reaction with N-acylhydrazines
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An efficient method has been developed for the synthesis of 4,6-dimethylpyridine-2,3-dicarbonitrile. A study was carried out on the reaction of this compound with N-acylhydrazines to give two structural isomers, namely, N′-(7-amino-2,4-dimethyl-5H-pyrrolo[3,4-b]pyridin-5-ylidene) carbohydrazides and N′-(5-amino-2,4-dimethyl-7H-pyrrolo[3,4-b]pyridin-7- ylidene)carbohydrazides as well as disubstituted N′,N″-(2,4- dimethyl-5H-pyrrolo[3,4-b]pyridine-5,7-diylidene)dicarbohydrazides.
- Rudenko,Kucherak,Tolmachev,Hordiyenko
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p. 964 - 969
(2012/03/26)
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- Pyrazole compounds and their use as antidiabetes agents
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The present invention provides a pyrazole compound that has liver glycogen phosphorylase inhibitory activity and is useful as a therapeutic or prophylactic agent for diabetes, the pyrazole compound represented by the following general formula (I): wherein Ring Q represents an aryl or heteroaromatic group, R1 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group or a C1-6 alkoxy group, R2 represents a halogen atom, a C1-6 alkyl group, a C1-6 alkoxy group or an azido group, R3 represents a halogen atom, a hydroxyl group, a C1-6 alkyl group, a halo C1-6 alkyl group, a C1-6 alkoxy group, an azido group, an amino group, an acylamino group or a C1-6 alkylsulfonylamino group, R4 and R5 are identical with or different from each other and represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a C3-8 cycloalkyl group, a substituted or unsubstituted saturated heterocyclic group, a substituted or unsubstituted aryl group, a C7-14 aralkyl group, a heteroaromatic group, or the like, or a pharmacologically acceptable salt thereof.
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- Reductive desulfurization of 3-cyano-2-methylthiopyridines under the action of Raney nickel
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The action of Raney nickel on substituted 3-cyano-2-methylthiopyridines was studied. Under conditions of catalytic hydrogenation, the reaction yields a mixture containing the aminosulfide resulting from reduction of the nitrile group with retention of the methylthio group, the nitrile resulting from elimination of the methylthio group, and the amine resulting from both reduction of the nitrile group and elimination of the methylthio group. Treatment of 3-cyano-2-methylthiopyridines with a large amount of Raney nickel under desulfurization conditions induces simultaneous elimination of the methylthio group and reduction of the nitrile group to the aminomethyl group. When reductive desulfurization is carried out in methanol or THF, primary amines are formed, while the reactions in isopropyl or ethyl alcohol give secondary or tertiary amines, which are formed upon alkylation of the amino group with alcohols.
- Zubarev,Zav'yalova,Litvinov
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p. 2578 - 2581
(2007/10/03)
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- The preparation of Some 4- and 5-Substituted Pyridine-2-carboxylic Acids as Fusaric Acid Analogues.
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In view of future studies on the structure-activity relationships involved in the inhibition of dopamine β-hydroxylase, the authors synthetized 5-substituted picolinic acids and 4-substituted fusaric acids selected by means of a random sampling procedure suited for small series.On this occasion, they succeeded in improving markedly the well-known synthesis of 5-nitropicolinic acid via a Rosenmund-v.Braun reaction with 2-bromo-5-nitropyridine. 5-Hydroxypicolinic acid which is easily accessible in the same way could be converted into 5-alkyloxypicolinic acids by reaction with alkyl halides in DMSO in the presence of silver oxide. 4-Substituted fusaric acids became accessible via 5-n-butyl-2-methyl-4-nitropyridine-N-oxide.
- Oehlke, J.,Schroetter, E.,Dove, S.,Schick, H.,Niedrich, H.
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p. 591 - 596
(2007/10/02)
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