33342-84-6Relevant academic research and scientific papers
Studies on Pyrimidine Derivatives. XXXII. Reaction of 4-Substituted 2,6-Dimethylpyrimidine 1-Oxides with Phosphoryl Chloride
Sakamoto, Takao,Yoshizawa, Hiroshi,Kaneda, Sohichi,Hama, Yoshiaki,Yamanaka, Hiroshi
, p. 4533 - 4538 (2007/10/02)
The reaction of 2,6-dimethyl-4-phenylpyrimidine 1-oxide with phosphoryl chloride gave 4-chloromethyl-2-methyl-6-phenylpyrimidine exclusively.In contrast, 2,6-dimethyl-4-methoxy-pyrimidine 1-oxide and 2,6-dimethyl-4-dimethylaminopyrimidine 1-oxide reacted with the same reagent to give the corresponding 2-chloromethylpyrimidines predominantly.Keywords - pyrimidine N-oxide; chloromethylpyrimidine; phosphoryl chloride; siteselective reaction; substituent effect
OXIDATION OF 2,4-DISUBSTITUTED PYRIMIDINES WITH ORGANIC PERACIDS
Yamanaka, Hiroshi,Ogawa, Shigeru,Sakamoto, Takao
, p. 573 - 576 (2007/10/02)
While 4,6-disubstituted (alkyl, aryl, alkoxyl) pyrimidines easily afforded the corresponding mono-N-oxides with hydrogen peroxide in glacial acetic acid, pyrimidine derivatives whose 6-position is free, are partly oxidatively degradated during N-oxidation reaction.The oxidation of the latter compounds under the above conditions gave 2,4-disubstituted imidazoles together with their mono-N-oxides.A likely mechanism of this ring-contraction and the improved conditions for the synthesis of the N-oxides are also described.
