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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 11, pp 1226–1231 | Cite as

N-alkylation of 1,4-dihydropyridine-3,5-dicarboxylic acid esters

  • A. É. Sausin'
  • V. K. Lusis
  • G. Ya. Dubur
  • Yu. I. Beilis
Article

Abstract

Alkylation of the anions of 1,4-dihydropyridines (1,4-DHP) formed by treatment of sodium hydride in aprotic solvents gave 1-alkyl(up to C6H13)-3,5-bis(ethoxycarbonyl)- and 1-alkyl-3,5-bis(aryloxycarbonyl)-1,4-DHP. The presence of a substituent in the 4 position increases the reactivity of the 1,4-DHP anion in the alkylation reaction. The absorption maximum in the UV spectra of the 1,4-DHP anion is shifted ∼100 nm bathochromically as compared with the neutral molecule. The longwave absorption maximum in the UV spectra of 1-alkyl-1,4-DHP is shifted hypsochromically as compared with the 1-unsubstituted compounds; this is explained by steric hindrance of the conjugation of the C=O groups with the π-electron system of the ring. The introduction of an alkyl group at the nitrogen atom facilitates the electrical oxidation of 1,4-DHP.

Keywords

Oxidation Ester Hydride Absorption Maximum Nitrogen Atom 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • A. É. Sausin'
    • 1
  • V. K. Lusis
    • 1
  • G. Ya. Dubur
    • 1
  • Yu. I. Beilis
    • 1
  1. 1.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga

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