A palladium-catalyzed coupling of 3-chloroquinoxalinones with various nitrogen-containing nucleophiles

Etienne Brachet; Jean François Peyrat; Jean Daniel Brion; Samir Messaoudi; Mouâd Alami

doi:10.1039/c3ob40338f

A palladium-catalyzed coupling of 3-chloroquinoxalinones with various nitrogen-containing nucleophiles

Etienne Brachet, Jean François Peyrat, Jean Daniel Brion, Samir Messaoudi, Mouâd Alami

Université Paris-Saclay

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

Abstract

An efficient and general palladium-catalyzed coupling of 3-chloro-quinoxalinones with a variety of nitrogen-containing nucleophiles such as (hetero)aromatic and aliphatic amides as well as some challenging weakly nucleophilic nitrogen compounds including lactams, carbamates and NH-containing azoles is described. In all cases, the reactions take place rapidly and cleanly in dioxane using Pd(OAc)₂ as a catalyst, Xantphos as a ligand and K₂CO₃ as a base furnishing the coupling 3-N-substituted quinoxalinone products in good to excellent yields.

Original language	English
Pages (from-to)	3808-3816
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	23
DOIs	https://doi.org/10.1039/c3ob40338f
Publication status	Published - 1 Jan 2013
Externally published	Yes

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title = "A palladium-catalyzed coupling of 3-chloroquinoxalinones with various nitrogen-containing nucleophiles",

abstract = "An efficient and general palladium-catalyzed coupling of 3-chloro-quinoxalinones with a variety of nitrogen-containing nucleophiles such as (hetero)aromatic and aliphatic amides as well as some challenging weakly nucleophilic nitrogen compounds including lactams, carbamates and NH-containing azoles is described. In all cases, the reactions take place rapidly and cleanly in dioxane using Pd(OAc)2 as a catalyst, Xantphos as a ligand and K2CO3 as a base furnishing the coupling 3-N-substituted quinoxalinone products in good to excellent yields.",

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doi = "10.1039/c3ob40338f",

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T1 - A palladium-catalyzed coupling of 3-chloroquinoxalinones with various nitrogen-containing nucleophiles

AU - Brachet, Etienne

AU - Peyrat, Jean François

AU - Brion, Jean Daniel

AU - Messaoudi, Samir

AU - Alami, Mouâd

PY - 2013/1/1

Y1 - 2013/1/1

N2 - An efficient and general palladium-catalyzed coupling of 3-chloro-quinoxalinones with a variety of nitrogen-containing nucleophiles such as (hetero)aromatic and aliphatic amides as well as some challenging weakly nucleophilic nitrogen compounds including lactams, carbamates and NH-containing azoles is described. In all cases, the reactions take place rapidly and cleanly in dioxane using Pd(OAc)2 as a catalyst, Xantphos as a ligand and K2CO3 as a base furnishing the coupling 3-N-substituted quinoxalinone products in good to excellent yields.

AB - An efficient and general palladium-catalyzed coupling of 3-chloro-quinoxalinones with a variety of nitrogen-containing nucleophiles such as (hetero)aromatic and aliphatic amides as well as some challenging weakly nucleophilic nitrogen compounds including lactams, carbamates and NH-containing azoles is described. In all cases, the reactions take place rapidly and cleanly in dioxane using Pd(OAc)2 as a catalyst, Xantphos as a ligand and K2CO3 as a base furnishing the coupling 3-N-substituted quinoxalinone products in good to excellent yields.

U2 - 10.1039/c3ob40338f

DO - 10.1039/c3ob40338f

M3 - Article

C2 - 23584212

AN - SCOPUS:84893481584

SN - 1477-0520

VL - 11

SP - 3808

EP - 3816

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 23

ER -

A palladium-catalyzed coupling of 3-chloroquinoxalinones with various nitrogen-containing nucleophiles

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