No abstract

SummaryThe interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino)prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate.

No abstract

2-(Ethoxymethylidene)-3-oxo carboxylic acid esters reacted with tetrazol-5-amine to give ethyl 4-alkyl-2-azidopyrimidine-5-carboxylates capable of undergoing subsequent nucleophilic substitution of hydrogen on C 6 or azido group. The reaction of ethyl 2-benzoyl-3-ethoxyprop-2-enoate with tetrazol-5-amine was accompanied by partial decomposition to afford a mixture of ethyl 3-oxo-3-phenylpropanoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate. Ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate was formed as a result of cyclization of diethyl 2-(ethoxymethylidene)propanedioate with tetrazol-5-amine.We examined the reactions of 2-(ethoxymethylidene)-3-oxo carboxylates 1 a -1 d and diethyl 2-(ethoxymethylidene)propanedioate (1e) with tetrazol-5-amine. Heating of 1a-1c with tetrazol-5-amine in boiling ethanol resulted in the formation of an inseparable mixture of products, whereas the reaction in

No abstract

No abstract

No abstract

A new route to aminocyclohexenones is reported.