Copper-catalyzed rearrangement of (Z)-propynal hydrazones via N-N bond cleavage

Itaru Nakamura, Naozumi Shiraiwa, Ryo Kanazawa, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)


Propynal hydrazones are successfully converted to the corresponding 3-aminoacrylonitriles in the presence of copper catalysts in good to high yields. As an example, (Z)-N-(hex-2-ynylidene)morpholin-4-amine reacted in the presence of 10 mol % Cu(OAc)2 in acetonitrile at 25 °C to afford (E)-3-morpholinohex-2-enenitrile ((E)-2 h) in 77% yield via C-N bond formation and subsequent β-elimination involving cleavage of N-N and C-H bonds.

Original languageEnglish
Pages (from-to)4198-4200
Number of pages3
JournalOrganic letters
Issue number18
Publication statusPublished - 2010 Sep 17

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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