84548-16-3

Upstream product

• 107-91-5 cyanoacetic acid amide 
• 41808-21-3 sodium salt of α-cyanoacetamide 
• 85302-08-5 2-((dimethylamino)methylene)-5-phenyl-cyclohexane-1,3-dione 
• 493-72-1 5-phenyl-cyclohexane-1,3-dione 
• 123-06-8 Ethoxymethylenemalononitrile 

Relevant academic research and scientific papers

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.

Syntheses with Nitriles, LXVII. - (Ethoxymethylene)malononitrile as Synthon for the Preparation of Fused Heterocyclic Pyrano and Pyrido Systems

(Ethoxymethylene)malononitrile (2) reacts with 4-hydroxy-2-quinolones 1a,b to give the pyranoquinolines 3a-c.With 4-hydroxycoumarin (4b) or its sodium salt 4a, dependent on the reaction conditions, the benzopyranopyridines 6a,b or the pyranobenzopyran 5a, respectively, are obtained.The carboxylic acid 7 is prepared by basic hydrolysis of 6a, dealkylated to give 8b by treatment with sulfuric acid, and after decarboxylation the benzopyranopyridine 9 can be obtained. 4-Hydroxy-6-methyl-2H-pyran-2-one reacts with 2 to give the pyranopyran derivative 10.Reaction of 1,3-cyclohexanediones with 2 affords the 5,6,7,8-tetrahydrobenzopyrans 11a-c.The fluorescent properties of 3, 5, 8a, 10, and 11 are discussed.

REACTION OF 2-FORMYL-1,3-CYCLOHEXANEDIONES WITH CYANOACETAMIDE

The condensation of salicylaldehyde and its analogs with cyanoacetamide to give iminocoumarins has been reported.