114969-48-1Relevant articles and documents
Regioselective Reaction of Heterocyclic N-Oxides, an Acyl Chloride, and Cyclic Thioethers
Frei, Przemyslaw,Heulyn Jones,Kay, Steven T.,McLellan, Jayde A.,Johnston, Blair F.,Kennedy, Alan R.,Tomkinson, Nicholas C. O.
, p. 1510 - 1517 (2018)
Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to a 74% isolated yield. The transformation can also be accomplished with alternative nitrogen containing heterocycles, including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation, diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.
Studies on Pyrimidine Derivatives. XXXIX. Site-Selectivity in the Reaction of 5-Substituted and 4,5-Disubstituted Pyrimidine N-Oxides with Trimethylsilyl Cynanide
Yamanaka, Hiroshi,Sakamoto, Takao,Nishimura, Sumiko,Sagi, Mataichi
, p. 3119 - 3126 (2007/10/02)
The site-selectivity in the modified Reissert-Henze reaction of 5-substituted and 4,5-disubstituted pyrimidine 1-oxides with trimethylsilyl cyanide was examined.The reaction of 5-substituted 4-methoxypyrimidine 1-oxides with trimethylsilyl cyanide gave exclusively 2-pyrimidinecarbonitriles in good yields without exception.On the other hand, the other 5-substituted and 4,5-disubstituted pyrimidine 1-oxides gave mainly 6-pyrimidinecarbonitriles.Keywords--site-selectivity; pyrimidine N-oxide; trimethylsilyl cyanide; Reissert-Henze reasction; pyrimidinecarbonitrile
