Effective 2,6-substitution of piperidine nitroxyl radical by carbonyl compound

Kiyoshi Sakai, Ken ichi Yamada, Toshihide Yamasaki, Yuichi Kinoshita, Fumiya Mito, Hideo Utsumi

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

Abstract

Nitroxyl radicals (nitroxides) with unpaired electron are widely used as antioxidants, contrast agents, and spin probes. Although piperidine nitroxyl radicals have many applications, these are mainly tetramethylpiperidine compounds, and only a few reports consider the substitution of N-O surround as a reaction site, such as 2,2,6,6-tetrasubstituted piperidine nitroxyl radicals. Our results revealed that the 2,6-position of the 2,2,6,6-tetramethylpiperidin-4-one compound was substituted by cyclohexyl groups to produce 2,2,6,6-tetrasubstituted piperidin-4-one derivatives under mild reaction conditions. An interesting result was obtained by using 15N-labeled NH4Cl instead of 14NH4Cl: it gave 15N-labeled 2,2,6,6-tetrasubstituted piperidin-4-one-1-oxyls with a high 15N content. In conclusion, the new method for the synthesis of nitroxyl radicals readily yields 2,2,6,6-tetrasubstituted piperidin-4-one under mild conditions.

Original languageEnglish
Pages (from-to)2311-2315
Number of pages5
JournalTetrahedron
Volume66
Issue number13
DOIs
Publication statusPublished - Mar 27 2010

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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