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Title: Synthesis of N-unsubstituted and N-methyl derivatives of 4-aryl-2,6-dimethyl-1,2-dihydropyridine-3,5-dicarbonitriles

Abstract

In the reduction of 2,6-dimethyl-4-arylpyridine-3,5-dicarbonitriles or their N-oxides by sodium borohydride, a mixture of 1,2- and 1,4-dihydropyridine-3,5-dicarbonitriles is formed. 1,2,6-Trimethyl-4-aryl-1,2-dihydropyridine-3,5-dicarbonitriles were obtained by reducing the corresponding pyridinium perchlorates or by alkylating 4-acryl-2,6-dimethyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives by methyl iodide.

Authors:
; ; ;
Publication Date:
Research Org.:
Institute of Organic Synthesis, Riga, USSR
OSTI Identifier:
5852082
Resource Type:
Journal Article
Resource Relation:
Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States); Journal Volume: 23:1; Other Information: Translated from Khim. Geterotsikl. Soedin.; 23: No. 1, 81-85(Jan 1987)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; 74 ATOMIC AND MOLECULAR PHYSICS; BOROHYDRIDES; CATALYTIC EFFECTS; METHYL IODIDE; NITRILES; NMR SPECTRA; SYNTHESIS; PYRIDINES; SODIUM COMPOUNDS; ALKYLATING AGENTS; CHEMICAL SHIFT; COUPLING CONSTANTS; INFRARED SPECTRA; J-J COUPLING; METHYLATION; MULTIPLETS; REDUCING AGENTS; REDUCTION; ULTRAVIOLET SPECTRA; ALKALI METAL COMPOUNDS; AZINES; BORON COMPOUNDS; CHEMICAL REACTIONS; COUPLING; HALOGENATED ALIPHATIC HYDROCARBONS; HETEROCYCLIC COMPOUNDS; HYDROGEN COMPOUNDS; INTERMEDIATE COUPLING; IODINATED ALIPHATIC HYDROCARBONS; ORGANIC COMPOUNDS; ORGANIC HALOGEN COMPOUNDS; ORGANIC IODINE COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; SPECTRA; 400201* - Chemical & Physicochemical Properties; 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory

Citation Formats

Zandersons, A.Z., Lusis, V.K., Mutsenietse, D.Kh., and Dubur, G.Ya. Synthesis of N-unsubstituted and N-methyl derivatives of 4-aryl-2,6-dimethyl-1,2-dihydropyridine-3,5-dicarbonitriles. United States: N. p., 1987. Web. doi:10.1007/BF00475478.
Zandersons, A.Z., Lusis, V.K., Mutsenietse, D.Kh., & Dubur, G.Ya. Synthesis of N-unsubstituted and N-methyl derivatives of 4-aryl-2,6-dimethyl-1,2-dihydropyridine-3,5-dicarbonitriles. United States. doi:10.1007/BF00475478.
Zandersons, A.Z., Lusis, V.K., Mutsenietse, D.Kh., and Dubur, G.Ya. 1987. "Synthesis of N-unsubstituted and N-methyl derivatives of 4-aryl-2,6-dimethyl-1,2-dihydropyridine-3,5-dicarbonitriles". United States. doi:10.1007/BF00475478.
@article{osti_5852082,
title = {Synthesis of N-unsubstituted and N-methyl derivatives of 4-aryl-2,6-dimethyl-1,2-dihydropyridine-3,5-dicarbonitriles},
author = {Zandersons, A.Z. and Lusis, V.K. and Mutsenietse, D.Kh. and Dubur, G.Ya.},
abstractNote = {In the reduction of 2,6-dimethyl-4-arylpyridine-3,5-dicarbonitriles or their N-oxides by sodium borohydride, a mixture of 1,2- and 1,4-dihydropyridine-3,5-dicarbonitriles is formed. 1,2,6-Trimethyl-4-aryl-1,2-dihydropyridine-3,5-dicarbonitriles were obtained by reducing the corresponding pyridinium perchlorates or by alkylating 4-acryl-2,6-dimethyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives by methyl iodide.},
doi = {10.1007/BF00475478},
journal = {Chem. Heterocycl. Compd. (Engl. Transl.); (United States)},
number = ,
volume = 23:1,
place = {United States},
year = 1987,
month = 7
}
  • The condensation of ethyl arylidenacetoacetate with cyanothioacetamide and of arylidenecyanothioacetamides with ethyl acetoacetate or of arylidenecyanothioacetamides with ethyl ..beta..-aminocrotonate gave 3-cyano-4-aryl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyridine-2-thiones. PMR spectroscopy showed that the 3-cyano-4-aryl-3,4-dihydro-pyridine-2-thiones are formed as a mixture of cis and trans isomers.
  • The stereospecific synthesis of the previously unknown retinoids (C/sub 15/ and C/sub 17/ aldehydes) rac-(2E,4E)-3-methyl-5-(2,6-dimethyl-6-ethoxycarbonyl-3-oxo-1-cyclohexenyl)-2,4-pentadienal and rac-(2E,4E,6E)-5-methyl-7-(2,6-dimethyl-6-ethoxycarbonyl-3-oxo-1-cyclohexenyl)-2,4,6-heptatrienal and their derivatives with dimedone was realized in order to study their biological activity.
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