Heterocyclic products from the oxidation of enamine and dienamine esters

ABSTRACT

N-alkylaminofumarates [1], Beta-aminocinnamates [2] and Beta-N-alkyl-aminocrotonates [3a] are oxidized by lead tetra-acetate [LTA] to give mixtures of acyclic oxidative dimers; in which enamine molecules are linked through their Beta-carbon atoms, as well as heterocyclic products pyrroles, pyridones and others [1,2,3] The above results promoted the present investigation of similar oxidations of ethyl [Z]-Beta-aminocrotonate [3b] and the dienamine esters, ethyl [Z], [E]-5- amino-4-carbethoxy-2, 4-hexadienoate [4] and methyl [Z], [E] -5-amino-4- car-bethoxy-3-carbmethoxy -2, 4-hexadienoate [5]