Open Access Open Access  Restricted Access Subscription Access

ROLE OF STERIC FACTORS IN INTRAMOLECULAR H-BOND FORMATION AND PECULIARITIES OF ELECTROCHEMICAL OXIDATION OF ETHYL 6-ALKYLSULFANYL-5-CYANO-2-METHYL-4-PHENYL-1,4-DIHYDROPYRIDINE-3-CARBOXYLATES

L. Baumane, A. Krauze, L. Krasnova, S. Belyakov, G. Duburs, J. Stradins
Cover Image

Abstract


6-Alkylsulfanyl-5-cyano-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylates containing electron-donating or electron-withdrawing groups were prepared by alkylation of 6-thioxo-1,4,5,6-tetrahydropyridine-3-carboxylate with alkyl halides. The H-bond formation in the case of 6-alkylsulfanyl substituent bearing sterically small hydrogen bond acceptor explains a partial lack of correlation of the electrochemical oxidation potentials with Taft's σ*-constants.

How to Cite
Baumane, L.; Krauze, A.; Krasnova, L.; Belyakov, S.; Duburs, G.; Stradiņš, J. Chem. Heterocycl. Compd. 2014, 49, 1623. [Khim. Geterotsikl. Soedin. 2013, 1752.]

For this article in the English edition see DOI 10.1007/s10593-014-1413-7


Keywords


6-alkylsulfanyl-5-cyano-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylates; electrochemical oxidation; hydrogen bonding; X-ray diffraction analysis

Full Text: PDF Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv