Copper(II)-catalyzed synthesis of pyrazinones from α-Azido-N- allylamides under an oxygen atmosphere

Line Zhang; Jian Yuan Lee; Naomi Yamazaki; Shunsuke Chiba

doi:10.1055/s-0030-1261185

Copper(II)-catalyzed synthesis of pyrazinones from α-Azido-N- allylamides under an oxygen atmosphere

Line Zhang, Jian Yuan Lee, Naomi Yamazaki, Shunsuke Chiba^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

A copper(II)-catalyzed reaction of -azido-N-allylamide synthetic under an oxygen atmosphere resulted in the formation of 2-formyl pyrazinones. The present transformation was characterized by the following steps: 1) 1,3-dipolar cycloaddition of the azido part onto the intramolecular alkene to give bicyclic aziridine intermediates; 2) further copper(II)-catalyzed oxygenation-oxidation of the aziridines to give 2-formyl pyrazinones.

Original language	English
Article number	D14511ST
Pages (from-to)	2167-2170
Number of pages	4
Journal	Synlett
Issue number	15
DOIs	https://doi.org/10.1055/s-0030-1261185
Publication status	Published - 2011
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

1,3-dipolar cycloaddition
copper
organic azides
oxygen
pyrazinone

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10.1055/s-0030-1261185

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title = "Copper(II)-catalyzed synthesis of pyrazinones from α-Azido-N- allylamides under an oxygen atmosphere",

abstract = "A copper(II)-catalyzed reaction of -azido-N-allylamide synthetic under an oxygen atmosphere resulted in the formation of 2-formyl pyrazinones. The present transformation was characterized by the following steps: 1) 1,3-dipolar cycloaddition of the azido part onto the intramolecular alkene to give bicyclic aziridine intermediates; 2) further copper(II)-catalyzed oxygenation-oxidation of the aziridines to give 2-formyl pyrazinones.",

keywords = "1,3-dipolar cycloaddition, copper, organic azides, oxygen, pyrazinone",

author = "Line Zhang and Lee, {Jian Yuan} and Naomi Yamazaki and Shunsuke Chiba",

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language = "English",

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T1 - Copper(II)-catalyzed synthesis of pyrazinones from α-Azido-N- allylamides under an oxygen atmosphere

AU - Zhang, Line

AU - Lee, Jian Yuan

AU - Yamazaki, Naomi

AU - Chiba, Shunsuke

PY - 2011

Y1 - 2011

N2 - A copper(II)-catalyzed reaction of -azido-N-allylamide synthetic under an oxygen atmosphere resulted in the formation of 2-formyl pyrazinones. The present transformation was characterized by the following steps: 1) 1,3-dipolar cycloaddition of the azido part onto the intramolecular alkene to give bicyclic aziridine intermediates; 2) further copper(II)-catalyzed oxygenation-oxidation of the aziridines to give 2-formyl pyrazinones.

AB - A copper(II)-catalyzed reaction of -azido-N-allylamide synthetic under an oxygen atmosphere resulted in the formation of 2-formyl pyrazinones. The present transformation was characterized by the following steps: 1) 1,3-dipolar cycloaddition of the azido part onto the intramolecular alkene to give bicyclic aziridine intermediates; 2) further copper(II)-catalyzed oxygenation-oxidation of the aziridines to give 2-formyl pyrazinones.

KW - 1,3-dipolar cycloaddition

KW - copper

KW - organic azides

KW - oxygen

KW - pyrazinone

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JF - Synlett

IS - 15

M1 - D14511ST

ER -

Copper(II)-catalyzed synthesis of pyrazinones from α-Azido-N- allylamides under an oxygen atmosphere

Abstract

ASJC Scopus Subject Areas

Keywords

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