Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines

Guangwu Zhang; Jinmin Miao; Yan Zhao; Haibo Ge

doi:10.1002/anie.201204339

Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines

Guangwu Zhang, Jinmin Miao, Yan Zhao, Haibo Ge

Chemistry and Biochemistry

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

109 Scopus citations

Abstract

O₂ leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives.

Original language	English
Pages (from-to)	8318-8321
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	33
DOIs	https://doi.org/10.1002/anie.201204339
State	Published - Aug 13 2012

Keywords

C-C coupling
copper
heterocycles
oxygen
synthetic methods

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abstract = "O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives.",

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author = "Guangwu Zhang and Jinmin Miao and Yan Zhao and Haibo Ge",

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T1 - Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones

T2 - Synthesis of cinnolines

AU - Zhang, Guangwu

AU - Miao, Jinmin

AU - Zhao, Yan

AU - Ge, Haibo

PY - 2012/8/13

Y1 - 2012/8/13

N2 - O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives.

AB - O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives.

KW - C-C coupling

KW - copper

KW - heterocycles

KW - oxygen

KW - synthetic methods

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DO - 10.1002/anie.201204339

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 33

ER -

Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines

Abstract

Keywords

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