52600-53-0

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
5-ACETYL-6-METHYL-2-OXO-1,2-DIHYDROPYRIDINE-3-CARBONITRILE is used as a research compound for exploring its potential medicinal properties. Its unique structure and reactivity make it a valuable candidate for the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 5-ACETYL-6-METHYL-2-OXO-1,2-DIHYDROPYRIDINE-3-CARBONITRILE is used as a building block or intermediate for the synthesis of more complex organic molecules. Its functional groups can be manipulated to form a variety of products.
Used in Chemical Reactions:
5-ACETYL-6-METHYL-2-OXO-1,2-DIHYDROPYRIDINE-3-CARBONITRILE is employed as a reactant in various chemical reactions, taking advantage of its reactivity to produce desired products or to study reaction mechanisms.

InChI:InChI=1/C9H8N2O2/c1-5-8(6(2)12)3-7(4-10)9(13)11-5/h3H,1-2H3,(H,11,13)

Upstream product

• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 123-54-6 acetylacetone 
• 107-91-5 cyanoacetic acid amide 
• 18856-72-9 3-dimethylaminomethylenepentane-2,4-dione 
• 18670-46-7 3-[(dimethylamino)methylenyl]-2,4-pentanedione 
• 41808-21-3 sodium salt of α-cyanoacetamide 
• 33884-41-2 ethoxylideneacetylacetone 

Downstream Products

• 121348-15-0 2-methyl-3-acetyl-5-cyano-6-chloro-pyridine 
• 860609-51-4 methyl 5-acetyl-3-amino-6-methylthieno[2,3-b]pyridine-2-carboxylate 
• 23616-29-7 1,6-naphthyridin-2(1H)-one 
• 88877-11-6 1,5-dimethyl-1,6-naphthyridin-2(1H)-one 
• 136117-46-9 5-acetyl-3-bromo-6-methyl-2(1H)-pyridinone 
• 5220-65-5 5-acetyl-6-methyl-2(1H)-pyridinone 
• 58405-00-8 5-acetyl-3-chloro-6-methyl-2(1H)-pyridinone 
• 139549-21-6 2-[(E)-2-(2-Benzyloxy-5-isopropenyl-6-methyl-pyridin-3-yl)-vinyl]-benzooxazole 
• 139549-19-2 2-(benzyloxy)-3-cyano-5-isopropenyl-6-methylpyridine 
• 139549-20-5 2-(benzyloxy)-5-isopropenyl-6-methylnicotinaldehyde 
• 88302-06-1 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarboxylic acid 
• 52600-60-9 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridine-carboxamide 
• 139549-18-1 2-(benzyloxy)-3-cyano-5-acetyl-6-methylpyridine 

Relevant academic research and scientific papers

5-substituted-3-oxadiazolyl-1,6-naphthyridin-2(1H)-one derivatives

A 5-substituted-3-oxadiazolyl-1,6-naphthyridin-2(1H)-one derivative of the formula (I): STR1wherein Het is oxadiazolyl, R 1 is H, lower alkyl, cyclo-lower alkyl, trifluoromethyl, lower alkenyl, lower alkynyl, lower alkoxy, lower alkoxy-lower alkyl, hydrox

Synthesis of 1-(β-D-glycopyranosyl)-3-deazapyrimidines from 2-hydroxy and 2-mercaptopyridines

The synthesis of new 4- and 5-substituted-3-cyanopyridine nucleosides has been performed by reacting the silylated pyridines and penta-O-aeetyl-α -Dglycopyranose in dichloroethane in the presence of SnCl4. The free nucleosides were tested for their potential activity against HIV and different types of tumor.

Synthesis of 2,3,5,6-tetrasubstituted pyridines from enamines derived from N,N-dimethylformamide dimethyl acetal

Reactions of 1,3-dicarbonyl compounds with N,N-dimethylformamide dimethyl acetal, followed by cyanothioacetamide or cyanoacetamide and sodium hydride, then acidification, give 5,6-disubstituted 3-cyanopyridine-2(1H)-thiones or 5,6-disubstituted 3-cyanopyridin-2(1H)-ones 4. Analogous reactions with the malononitrile dimer give 5,6-disubstituted 3-cyano-2-(dicyanomethylene)-1,2-dihydropyridines 9.

Novel alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones

This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.

Pyridone esters as inotropic agents

Described are compounds of the formula STR1 wherein R is hydrogen, lower alkyl, halo, cyano, hydroxy, amino, lower alkylamino, --CH2 NH2, --CH2 OH or --COOR"; R' is hydrogen, lower cycloalkyl or lower alkyl; R' is lower alkenyl, lower alkynyl, lower cycloalkyl, --(W)n Y wherein W is straight or branched chain lower alkyl or lower alkenyl, n is 0 to 5, and Y is Ar, lower cycloalkyl, lower alkenyl, lower alkynyl, --COOZ wherein Z is lower alkyl, STR2 or NAB wherein A and B are, independently, lower alkyl, benzyl or substituted benzyl, and Ar is 2, 3 or 4-pyridyl, pyridazinyl, pyrimidinyl, quinolyl, isoquinolyl, phthalazinyl, quinazolinyl, thiazolyl, phenyl, benzyl, furyl, tetrahydrofuryl or thienyl, unsubstituted or substituted with lower alkyl, lower alkoxy, halo, amino, or --CF3 ; R"' is --COOR", STR3 and X is oxygen or nitrogen; or a pharmaceutically acceptable salt thereof, and their use in the treatment of impaired ventricular myocardial contractility. The compounds exhibit cardiotonic activity.

5-Acyl-2-(1H)-pyridinones

Novel 5-acyl-2-(1H)pyridinones and their use as cardiotonic agents. Typical of the compounds is 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile which is prepared by condensing anionic cyano acetamide with 3-[(dimethylamino)methylenyl]-2,4-penta

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles.V. Synthesis of 5-Acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles and 1,2,5,6,7,8-Hexahydro-2,5-dioxo-3-quinolinecarboxamides

The reaction of open-chain sym-2-dimethylaminomethylene-1,3-diones Ia-d with sodium cyanoacetamide gave, generally in good yields, 6-substituted 5-acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles IIa-d, whereas cyclohexane sym-2-dimethylaminomethylene-1,3-diones Ie-h afforded in general a mixture of 1,2,5,6,7,8-hexahydro-2,5-dioxo-3-quinolinecarbonitriles and 5,6,7,8-tetrahydro-2,5-dioxo-2H-1-benzopyran-3-carboxamides, the latter being isolated in two cases.The reaction of Ie-h with cyanoacetamide in refluxing anhydrous ethanol gave 1,2,5,6,7,8-hexahydro-2,5-dioxo-3-quinolinecarboxamides IIIe-h in excellent yields, whereas Ia-d did not react with the exception of Ia which afforded in good yield 3-pyridinecarboxamide IIIa.Other 3-pyridinecarboxamides were obtained by partial hydrolysis of nitriles IIb,d. 3-Pyridine and 3-quinoline carboxamides were hydrolyzed in satisfactory yields with hydrochloric acid to the corresponding carboxylic acids, which were decarboxylated in good yields to 5-acyl-2(1H)-pyridinones and 7,8-dihydro-2,5-(1H,6H)-quinolinediones, respectively, by reflux in quinoline containing a catalytic amount of copper powder.

5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their cardiotonic use

4-R2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III), Q is CN) or corresponding 4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.

5-Alkyl-1,6-naphthyridin-2(1H)-ones and cardiotonic use thereof

1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic ag