Collect. Czech. Chem. Commun.
1979, 44, 3288-3295
https://doi.org/10.1135/cccc19793288
Structure of reaction product of 3-aminocrotononitrile with esters of alkoxymethylenecyanoacetic acid
Dušan Ilavskýa, Václav Jehličkab and Josef Kuthanc
a Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava
b Department of Physical Chemistry, Prague Institute of Chemical Technology, 166 28 Prague
c Department of Organic Chemistry
Abstract
Study of dipole moments of 3,5-dicyanopyrridine derivatives II-IV has shown that cyclocondensation of 3-aminocrotononitrile with esters of alkoxymethylenecyanoacetic acid gives the2-pyridone derivative I which can be transformed in 2-chloro- or 2-bromo derivatives IV and V by action of the respective halogenation agents. The substance IV is conversed into 2-iodo- and 2-dimethylamino derivatives VI and VII on action of HI and dimethylformamide, respectively. Alkylation of the 2-pyridone I with methyl iodide takes place at nitrogen atom to give the compound IX. The 1,4-dihydropyridine derivative X has been obtained by action of NaBH4 on IV.
