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

Itaru Nakamura; Naozumi Shiraiwa; Ryo Kanazawa; Masahiro Terada

doi:10.1021/ol1017504

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

Itaru Nakamura, Naozumi Shiraiwa, Ryo Kanazawa, Masahiro Terada

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

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 language	English
Pages (from-to)	4198-4200
Number of pages	3
Journal	Organic letters
Volume	12
Issue number	18
DOIs	https://doi.org/10.1021/ol1017504
Publication status	Published - 2010 Sep 17

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Copper-catalyzed rearrangement of (Z)-propynal hydrazones via N-N bond cleavage",

abstract = "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.",

author = "Itaru Nakamura and Naozumi Shiraiwa and Ryo Kanazawa and Masahiro Terada",

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T1 - Copper-catalyzed rearrangement of (Z)-propynal hydrazones via N-N bond cleavage

AU - Nakamura, Itaru

AU - Shiraiwa, Naozumi

AU - Kanazawa, Ryo

AU - Terada, Masahiro

PY - 2010/9/17

Y1 - 2010/9/17

N2 - 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.

AB - 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.

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