Reaction of γ‐Nitroketones and Methyl 4‐Nitrobutanoates with Formaldehyde and Primary Amines.

Abstract

Pyrimidine derivatives R 0510Reaction of γ-Nitroketones and Methyl 4-Nitrobutanoates with Formaldehyde and Primary Amines. -Condensation of sterically non-hindered 5-nitropentan-2-one with Me-NH2 and formaldehyde affords pyrimidinylcarbonyl-substituted diazabicyclononane (VII) in one experimental stage. Similar reaction of 4-nitrobutanoates (I) stops after formation of hexahydropyrimidines (IV). -(SHAKIROV*, R. R.; VLASOVA, L. I.; SHISHKIN, D. V.; YARMUKHAMEDOV, N. N.; BAYBULATOVA, N. Z.; SEMESKO, D. G.; DOKICHEV, V. A.; TOMILOV, Y. V.; Russ.

Methyl nitroacetate and 3-nitropropionate in the synthesis of hexahydropyrimidines and piperidines

“…In the case of methyl nitroacetate both the 5-nitrohexahydropyrimidine and isomeric 3,5-di(methoxycarbonyl)-1-methyl-3,5-dinitropiperidines are formed.The reaction of primary amines and formaldehyde with compounds containing a mobile hydrogen atom on a carbon atom is widely used in organic synthesis as a convenient method for preparing tetrahydro-1,3-oxazines, hexahydropyrimidines [1, 2], and also 3-aza-[3-6] and 3,7-diazabicyclo[3,3,1]nonanes [3,[7][8][9][10][11][12][13][14][15]. Members of this class of compounds show high physiological activity and are used in medical practice as antimicrobial, antiviral, antitumor and other medicinal agents [10][11][12]16].…”