61885-21-0Relevant academic research and scientific papers
Nucleophilic ring-opening of the azole and azine moieties in 6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-ones
Ulomsky,Voronin,Rusinov,Chupakhin
, p. 682 - 688 (2007/10/03)
The effects of the nature of the nucleophile and the structure of 6-nitrotriazolo[1,5-a]pyrimidinones on the direction of the ring opening were investigated. The triazole ring is opened under the action of strong bases, such as alkoxides or alkalis, to form 2-cyanoaminopyrimidinones and then 2-aminopyrimidinones. The results of the reactions with N-nucleophiles depend on the accessibility of position 5 of the heterocycle. Thus, sterically hindered secondary amines react with 5-methyltriazolopyrimidinones to give 2-guanidinopyrimidinones and then 2-aminopyrimidinones. In the absence of a substituent at position 5, the azine ring is opened to form 4-alkyl-3-amino-1,2,4-triazoles and 3-amino-2-nitroacrylamides. Under the action of primary amines, only the pyrimidine fragment is cleaved.
Pyrimidine Derivatives and Related Compounds. Part 41. Reactions of 1,3,6-Trimethyl-5-nitrouracil and its 6-Bromomethyl Analogue with Amines and Hydrazines. Synthesis of Pyrazolopyrimidine N-Oxides and their Ring Expansion to Pyrimidopyrimid
Hirota, Kosaku,Yamada, Yoshihiro,Asao, Tetsuji,Senda, Shigeo
, p. 277 - 284 (2007/10/02)
Reactions of 1,3,6-trimethyl-5-nitrouracil (1) and 6-bromomethyl-1,3-dimethyl-5-nitrouracil (4) with amines and hydrazines have been studied with the aim of synthesising fused-ring pyrimidines.Treatment of compound (4) with primary amines afforded 2-subst
