Reaction of ethyl acetoacetate with formaldehyde and primary amines

Effect of aliphatic alcohols on the reaction of acetoacetic ester with formaldehyde and primary amines

“…Physicochemical constants of compounds Iа, Ib [4], IIа, IIb [4], IIIа, IIIb [32], and IV [32] coincided with the literature data.…”

“…The synthesized nitrogen heterocycles I-IV were isolated by preparative TLC and characterized by 1 Н and 13 С spectra [4,32].…”

“…Earlier, we have shown that the reaction of acetoacetic ester with formaldehyde and primary amines in aqueous-alcoholic media leads to alkyl-5-acetyl-1,3dimethylhexahydropyrimidine-5-carboxylates and alkyl-1,3-dimethylhexahydropyrimidine-5-carboxylates [4]. Hitherto, the effect of the nature of the hemiacetal derivatives of formaldehyde on the reaction of their condensation with acetoacetic ester and primary amines was not discussed.…”

“…Formaldehyde and primary amines are widely used in organic synthesis for preparation of tetrahydro-1,3oxazines [1,2], hexahydropyrimidines [1][2][3][4][5][6], 3-azaand 3,7-diazabicyclo[3.3.1]nonanes [7][8][9][10][11][12], as well as 1,3,5-hexahydrotriazines [13]. Specimens of compounds of this series possess a wide spectrum of biological activity [14][15][16][17] (antimicrobial, antiviral, antitumor, etc.)…”

A concise route to 4-aminomethylpyrazoles and 4-aminomethylisoxazoles from acetylacetone-derived hexahydropyrimidines under mild conditions

“…However, recent reports have introduced highyielding procedures for the reaction of ethyl acetoacetate with formaldehyde and primary amines to furnish the corresponding hexahydropyrimidines in comparable yields (Latypova et al, 2013;Mukhopadhyay et al, 2011). HHP-ETAA conjugates (Saleh et al, 2014) have shown a different mechanism when treated with hydrazine and, subsequently, different products were obtained (Fig.…”