One-pot synthesis of fluorinated 2-amino-pyrimidine-N-oxides. Competing pathways in the four-atom side-chain rearrangements of 1,2,4-oxadiazoles

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Abstract

Trifluoromethylated 2-amino-pyrimidine N-oxides have been synthesized by reaction of the 3-amino-5-methyl-1,2,4-oxadiazolewith trifluoromethyl-b-diketones in the presence of perchloric acid, followed by hydrolysis. In this ring-to-ring transformation an initialformation of (unisolated) 1,2,4-oxadiazole-pyrimidinium salts, and subsequent ring-opening at the oxadiazole moiety occurs. Isolation of2-(hydroxyamino)-pyrimidine from the reaction mixture evidenced the presence of a competing pathway where the N(4) nitrogen of theoxadiazole is involved in the formation of a regioisomeric pyrimidinium salt. The effect of the trifluoromethyl group on the productdistribution is discussed. By X-ray analysis, the crystal structure of two different N-oxide regioisomers has been unambiguously ascertained.
Original languageEnglish
Pages (from-to)1158-1164
Number of pages7
JournalTetrahedron
Volume62
Publication statusPublished - 2006

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Biochemistry
  • Drug Discovery

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