N-Allenylnitrone acts as 2-azadiene in the Cu-catalyzed cascade reaction of O-propargylic oximes with azodicarboxylates

Itaru Nakamura; Takeru Jo; Dong Zhang; Masahiro Terada

doi:10.1039/c4qo00156g

N-Allenylnitrone acts as 2-azadiene in the Cu-catalyzed cascade reaction of O-propargylic oximes with azodicarboxylates

Itaru Nakamura, Takeru Jo, Dong Zhang, Masahiro Terada

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

13 Citations (Scopus)

Abstract

The reaction of O-propargylic oximes with azodicarboxylates efficiently afforded 1,2,4-triazine oxides in good yields. The key intermediate, N-allenylnitrone, acted as 2-azadiene, undergoing stepwise [4 + 2] cycloaddition.

Original language	English
Pages (from-to)	914-918
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	1
Issue number	8
DOIs	https://doi.org/10.1039/c4qo00156g
Publication status	Published - 2014 Oct 1

ASJC Scopus subject areas

Organic Chemistry

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10.1039/c4qo00156g

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abstract = "The reaction of O-propargylic oximes with azodicarboxylates efficiently afforded 1,2,4-triazine oxides in good yields. The key intermediate, N-allenylnitrone, acted as 2-azadiene, undergoing stepwise [4 + 2] cycloaddition.",

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AU - Jo, Takeru

AU - Zhang, Dong

AU - Terada, Masahiro

N1 - Publisher Copyright: This journal is © the Partner Organisations 2014.

PY - 2014/10/1

Y1 - 2014/10/1

N2 - The reaction of O-propargylic oximes with azodicarboxylates efficiently afforded 1,2,4-triazine oxides in good yields. The key intermediate, N-allenylnitrone, acted as 2-azadiene, undergoing stepwise [4 + 2] cycloaddition.

AB - The reaction of O-propargylic oximes with azodicarboxylates efficiently afforded 1,2,4-triazine oxides in good yields. The key intermediate, N-allenylnitrone, acted as 2-azadiene, undergoing stepwise [4 + 2] cycloaddition.

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N-Allenylnitrone acts as 2-azadiene in the Cu-catalyzed cascade reaction of O-propargylic oximes with azodicarboxylates

Abstract

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