137347-43-4

Upstream product

• 90961-43-6 2-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester 
• 105-45-3 acetoacetic acid methyl ester 
• 587-04-2 m-Chlorobenzaldehyde 
• 147597-24-8 4-(3-Chloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-methyl ester 

Relevant academic research and scientific papers

Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetrical 1,4-dihydropyridine dicarboxylates

Several 3-(2-cyanoethyl)-1,4-dihydropyridine carboxylates (16) were prepared in moderate to good yields by means of the Hantzsch reaction. Treatment of these carboxylates with a weak base such as sodium sulfide or tetrabutylammonium fluoride at room temperature afforded smoothly the corresponding 1,4-dihydropyridine monocarboxylic acids (18) in good yields. The monocarboxylic acids 18n and 18o were esterified with 2-nitrooxypropanol or N-(2-hydroxyethyl)nicotinamide p-toluenesulfonic acid salt to afford the selective coronary vasodilators CD-349 (5) and CD-832 (6), respectively.

Synthesis and antihypertensive activities of new 1,4-dihydropyridine derivatives containing a nitrooxy moiety at the 3-ester position

The synthesis of a new series of dihydropyridines containing a nitrooxy moiety at the 3-ester position is described. The antihypertensive activity of the compounds was examined and compared with that of nifedipine; some of them were relatively potent. The structure-activity relationship is also discussed.

Process for preparation of enantiomerically pure polysubstituted 1,4-dihydropyridines

A process for the optical resolution of racemic 1,4-dihydropyridines, containing isothioureido groups. Salification of racemic isothioureas with optically active acids produces diasteroisomeric mixtures of isothiouronium salts, that, using conventional techniques, are separated in the individual components to give optically pure isothioureides of 1,4-dihydropyridines and salts thereof with conventional acids. Said optically pure 1,4-dihydropyridines can then be subjected to desulphuration and to different transformations to give to other enantiomerically pure and therapeutically useful 1,4-dihydropyridines.

Resolution of 1,4-dihydropyridine derivatives

Optically active compounds of formula 1 STR1 wherein R1 is H or lower alkyl; R2 and R6 are each independently lower alkyl, aryl, or arylalkyl; R3 is CN, NO2, CO2 R5, CONHR5, SO2 R5, or P(O)(OR5)2, where R5 is lower alkyl, lower alkoxyalkyl, aryl, or arylalkyl; R4 is aryl, heterocyclyl, or fused-ring heterocyclyl, optionally substituted with one, two, or three halo, NO2, CN, lower alkyl, lower alkoxy, lower alkylamino, CF3, OCH2 F, or OCF3 ; are prepared by fractional crystallization from hot organic solvent and water in the presence of a suitable optically active amine base.