Alkyl 5-aryl-7-methyl-1,5-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylates were obtained by melting acetoacetic acid esters with 5-aminotetrazole and aromatic aldehyde.
Scheme 1.It was established formerly that the reaction of ketoacid esters with a mixture of an aromatic aldehyde and a 5-aminotetrazole or 3-amino-1,2,4-triazole resulted in the formation of fused heterocyclic systems [1]. For instance, methyl pyruvates reacted with a mixture of an aromatic aldehyde and a 5-aminotetrazole [2, 3] or 3-amino-1,2,4-triazole [4] to give methyl 5-aryl-6-acyl-7-methoxycarbonyl-1,5-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylates and methyl 5-aryl-6-acyl-7-methoxycarbonyl-1,5-dihydrotriazolo[1,5-a]pyrimidine-6-carboxylates respectively.Aiming at the preparation of new alkyl 1,5-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylates, at estimation of the effect of the substituent in the ester group on the course of the reaction and at the establishment of the spatial arrangement of compounds obtained we investigated the reaction of various acetoacetic acid esters with the mixture of 5-amino-tetrazole and aromatic aldehydes.The study showed that at the melting of equimolar amounts of the initial reagents at 130-170°C over 20-30 min a single product was obtained, alkyl 5-aryl-7-
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