An expeditious copper-catalyzed access to 3-aminoquinolinones, 3-aminocoumarins and anilines using sodium azide

Samir Messaoudi; Jean Daniel Brion; Mouâd Alami

doi:10.1002/adsc.201000149

An expeditious copper-catalyzed access to 3-aminoquinolinones, 3-aminocoumarins and anilines using sodium azide

Samir Messaoudi
, Jean Daniel Brion
, Mouâd Alami

Université Paris-Saclay
Univ Paris-Sud

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

77 Citations (Scopus)

Abstract

An efficient copper-catalyzedin in situ C-(sp²)-NH₂ bond formation to provide a range of 3-aminoquinolin-2(1H)-ones and 3-aminocoumarins from 3-bromoquinolinones and 3-bromocoumarins, respectively, has been achieved. The reaction conditions involve the use of copper powder as the catalyst, eco-friendly ethanol as the solvent in the pres ence of pipecolinic acid as the ligand and ascorbic acid as the additive. The efficiency of this practical method was demonstrated in the synthesis of various anilines.

Original language	English
Pages (from-to)	1677-1687
Number of pages	11
Journal	Advanced Synthesis and Catalysis
Volume	352
Issue number	10
DOIs	https://doi.org/10.1002/adsc.201000149
Publication status	Published - 5 Jul 2010
Externally published	Yes

Keywords

Aminoheterocycles
Anilines
C-N bond formation
Copper catalysis
Sodium azide

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10.1002/adsc.201000149

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title = "An expeditious copper-catalyzed access to 3-aminoquinolinones, 3-aminocoumarins and anilines using sodium azide",

abstract = "An efficient copper-catalyzedin in situ C-(sp2)-NH2 bond formation to provide a range of 3-aminoquinolin-2(1H)-ones and 3-aminocoumarins from 3-bromoquinolinones and 3-bromocoumarins, respectively, has been achieved. The reaction conditions involve the use of copper powder as the catalyst, eco-friendly ethanol as the solvent in the pres ence of pipecolinic acid as the ligand and ascorbic acid as the additive. The efficiency of this practical method was demonstrated in the synthesis of various anilines.",

keywords = "Aminoheterocycles, Anilines, C-N bond formation, Copper catalysis, Sodium azide",

author = "Samir Messaoudi and Brion, \{Jean Daniel\} and Mou{\^a}d Alami",

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T1 - An expeditious copper-catalyzed access to 3-aminoquinolinones, 3-aminocoumarins and anilines using sodium azide

AU - Messaoudi, Samir

AU - Brion, Jean Daniel

AU - Alami, Mouâd

PY - 2010/7/5

Y1 - 2010/7/5

N2 - An efficient copper-catalyzedin in situ C-(sp2)-NH2 bond formation to provide a range of 3-aminoquinolin-2(1H)-ones and 3-aminocoumarins from 3-bromoquinolinones and 3-bromocoumarins, respectively, has been achieved. The reaction conditions involve the use of copper powder as the catalyst, eco-friendly ethanol as the solvent in the pres ence of pipecolinic acid as the ligand and ascorbic acid as the additive. The efficiency of this practical method was demonstrated in the synthesis of various anilines.

AB - An efficient copper-catalyzedin in situ C-(sp2)-NH2 bond formation to provide a range of 3-aminoquinolin-2(1H)-ones and 3-aminocoumarins from 3-bromoquinolinones and 3-bromocoumarins, respectively, has been achieved. The reaction conditions involve the use of copper powder as the catalyst, eco-friendly ethanol as the solvent in the pres ence of pipecolinic acid as the ligand and ascorbic acid as the additive. The efficiency of this practical method was demonstrated in the synthesis of various anilines.

KW - Aminoheterocycles

KW - Anilines

KW - C-N bond formation

KW - Copper catalysis

KW - Sodium azide

U2 - 10.1002/adsc.201000149

DO - 10.1002/adsc.201000149

M3 - Article

AN - SCOPUS:77954776890

SN - 1615-4150

VL - 352

SP - 1677

EP - 1687

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 10

ER -

An expeditious copper-catalyzed access to 3-aminoquinolinones, 3-aminocoumarins and anilines using sodium azide

Abstract

Keywords

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