Rapid access to 3-(N-substituted)-aminoquinolin-2(1H)-ones using palladium-catalyzed C-N bond coupling reaction

Samir Messaoudi; Davide Audisio; Jean Daniel Brion; Mouâd Alami

doi:10.1016/j.tet.2007.07.085

Rapid access to 3-(N-substituted)-aminoquinolin-2(1H)-ones using palladium-catalyzed C-N bond coupling reaction

Samir Messaoudi, Davide Audisio, Jean Daniel Brion, Mouâd Alami

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

Abstract

A series of 3-(N-substituted)-aminoquinolin-2(1H)-ones have been synthesized by the palladium-catalyzed C-N coupling reaction starting from 3-bromoquinolin-2-(1H)-ones. Various nucleophiles including amines, amides, sulfonamides, carbamates and ureas have been used successfully. In all the cases, the reactions take place rapidly in 1,4-dioxane and proceed in good to excellent yield using palladium acetate as a catalyst, Xantphos as a ligand and Cs₂CO₃ as a base.

Original language	English
Pages (from-to)	10202-10210
Number of pages	9
Journal	Tetrahedron
Volume	63
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2007.07.085
Publication status	Published - 8 Oct 2007

Keywords

3-(N-Substituted)-aminoquinolin-2-(1H)-ones
Bromoquinolin-2-(1H)-ones
C-N bond coupling reaction
Palladium

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10.1016/j.tet.2007.07.085

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title = "Rapid access to 3-(N-substituted)-aminoquinolin-2(1H)-ones using palladium-catalyzed C-N bond coupling reaction",

abstract = "A series of 3-(N-substituted)-aminoquinolin-2(1H)-ones have been synthesized by the palladium-catalyzed C-N coupling reaction starting from 3-bromoquinolin-2-(1H)-ones. Various nucleophiles including amines, amides, sulfonamides, carbamates and ureas have been used successfully. In all the cases, the reactions take place rapidly in 1,4-dioxane and proceed in good to excellent yield using palladium acetate as a catalyst, Xantphos as a ligand and Cs2CO3 as a base.",

keywords = "3-(N-Substituted)-aminoquinolin-2-(1H)-ones, Bromoquinolin-2-(1H)-ones, C-N bond coupling reaction, Palladium",

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

year = "2007",

month = oct,

day = "8",

doi = "10.1016/j.tet.2007.07.085",

language = "English",

volume = "63",

pages = "10202--10210",

journal = "Tetrahedron",

issn = "0040-4020",

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TY - JOUR

T1 - Rapid access to 3-(N-substituted)-aminoquinolin-2(1H)-ones using palladium-catalyzed C-N bond coupling reaction

AU - Messaoudi, Samir

AU - Audisio, Davide

AU - Brion, Jean Daniel

AU - Alami, Mouâd

PY - 2007/10/8

Y1 - 2007/10/8

N2 - A series of 3-(N-substituted)-aminoquinolin-2(1H)-ones have been synthesized by the palladium-catalyzed C-N coupling reaction starting from 3-bromoquinolin-2-(1H)-ones. Various nucleophiles including amines, amides, sulfonamides, carbamates and ureas have been used successfully. In all the cases, the reactions take place rapidly in 1,4-dioxane and proceed in good to excellent yield using palladium acetate as a catalyst, Xantphos as a ligand and Cs2CO3 as a base.

AB - A series of 3-(N-substituted)-aminoquinolin-2(1H)-ones have been synthesized by the palladium-catalyzed C-N coupling reaction starting from 3-bromoquinolin-2-(1H)-ones. Various nucleophiles including amines, amides, sulfonamides, carbamates and ureas have been used successfully. In all the cases, the reactions take place rapidly in 1,4-dioxane and proceed in good to excellent yield using palladium acetate as a catalyst, Xantphos as a ligand and Cs2CO3 as a base.

KW - 3-(N-Substituted)-aminoquinolin-2-(1H)-ones

KW - Bromoquinolin-2-(1H)-ones

KW - C-N bond coupling reaction

KW - Palladium

U2 - 10.1016/j.tet.2007.07.085

DO - 10.1016/j.tet.2007.07.085

M3 - Article

AN - SCOPUS:34548201780

SN - 0040-4020

VL - 63

SP - 10202

EP - 10210

JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

Rapid access to 3-(N-substituted)-aminoquinolin-2(1H)-ones using palladium-catalyzed C-N bond coupling reaction

Abstract

Keywords

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