THE SYNTHESIS AND TRANSFORMATIONS OF ETHYL (Z)-2-[2,2-BIS(ETHOXYCARBONYL)VINYL]AMINO-3-DIMETHYLAMINOPROPENOATE, A NEW REAGENT IN THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS

Ethyl (Z)-2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-dimethylaminopropenoate (5), a new reagent in the synthesis of heteroaryl substituted beta-amino-alpha,beta- -dehydro-amino acid derivatives and some fused heterocyclic systems, was prepared from ethyl N-2,2-bis(ethoxycarbonyl)vinylglycinate (3) and N,N-dimethylformamide dimethyl acetal (4). The substitution of the dimethylamino group in the compound 5 with heterocyclic amines produced ethyl 2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-heteroarylaminopropenoates 7a-f and, in some instances, [2,2-bis-(ethoxycarbonyl)vinyl]aminoazolo- or -azinopyrimidine derivatives 8g-k.