Alkylation of 3,5-dichloro-2(1H)-pyrazinones using malonate esters

Nigam M. Mishra; Vsevolod A. Peshkov; Olga P. Pereshivko; Sachin G. Modha; Erik V. Van Der Eycken

doi:10.1016/j.tetlet.2012.06.080

Alkylation of 3,5-dichloro-2(1H)-pyrazinones using malonate esters

Nigam M. Mishra, Vsevolod A. Peshkov, Olga P. Pereshivko, Sachin G. Modha, Erik V. Van Der Eycken

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

4 Citations (Scopus)

Abstract

An efficient base-promoted 3-alkylation of 3,5-dichloro-2(1H)-pyrazinones with various malonate esters is described. The method constitutes a simple example of a C-C bond forming process at the 3-position of the pyrazinone core allowing to attain 3-substituted pyrazinones in good to high yields. 3-Alkylation of 3,5-dichloro-2(1H)-pyrazinones with acetoacetic ester was accompanied by further retro-Claisen fragmentation.

Original language	English
Pages (from-to)	4676-4678
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2012.06.080
Publication status	Published - Aug 29 2012
Externally published	Yes

Keywords

3,5-Dichloro-2(1H)-pyrazinones
Acetoacetic ester
Heterocycles
Malonate ester

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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title = "Alkylation of 3,5-dichloro-2(1H)-pyrazinones using malonate esters",

abstract = "An efficient base-promoted 3-alkylation of 3,5-dichloro-2(1H)-pyrazinones with various malonate esters is described. The method constitutes a simple example of a C-C bond forming process at the 3-position of the pyrazinone core allowing to attain 3-substituted pyrazinones in good to high yields. 3-Alkylation of 3,5-dichloro-2(1H)-pyrazinones with acetoacetic ester was accompanied by further retro-Claisen fragmentation.",

keywords = "3,5-Dichloro-2(1H)-pyrazinones, Acetoacetic ester, Heterocycles, Malonate ester",

author = "Mishra, {Nigam M.} and Peshkov, {Vsevolod A.} and Pereshivko, {Olga P.} and Modha, {Sachin G.} and {Van Der Eycken}, {Erik V.}",

year = "2012",

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language = "English",

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T1 - Alkylation of 3,5-dichloro-2(1H)-pyrazinones using malonate esters

AU - Mishra, Nigam M.

AU - Peshkov, Vsevolod A.

AU - Pereshivko, Olga P.

AU - Modha, Sachin G.

AU - Van Der Eycken, Erik V.

PY - 2012/8/29

Y1 - 2012/8/29

N2 - An efficient base-promoted 3-alkylation of 3,5-dichloro-2(1H)-pyrazinones with various malonate esters is described. The method constitutes a simple example of a C-C bond forming process at the 3-position of the pyrazinone core allowing to attain 3-substituted pyrazinones in good to high yields. 3-Alkylation of 3,5-dichloro-2(1H)-pyrazinones with acetoacetic ester was accompanied by further retro-Claisen fragmentation.

AB - An efficient base-promoted 3-alkylation of 3,5-dichloro-2(1H)-pyrazinones with various malonate esters is described. The method constitutes a simple example of a C-C bond forming process at the 3-position of the pyrazinone core allowing to attain 3-substituted pyrazinones in good to high yields. 3-Alkylation of 3,5-dichloro-2(1H)-pyrazinones with acetoacetic ester was accompanied by further retro-Claisen fragmentation.

KW - 3,5-Dichloro-2(1H)-pyrazinones

KW - Acetoacetic ester

KW - Heterocycles

KW - Malonate ester

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