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.}",

note = "Funding Information: Support was provided by the Fund for Scientific Research (FWO), Flanders and by the Research Fund of the University of Leuven (KU Leuven). N.M.M. is grateful to EMECW13 (Erasmus Mundus External Cooperation Window Lot 13 India) for obtaining a doctoral scholarship. V.A.P. is grateful to the EMECW (Triple I) for obtaining a doctoral scholarship. The authors thank Ir. B. Demarsin for valuable help with HRMS. Copyright: Copyright 2012 Elsevier B.V., All rights reserved.",

year = "2012",

month = aug,

day = "29",

doi = "10.1016/j.tetlet.2012.06.080",

language = "English",

volume = "53",

pages = "4676--4678",

journal = "Tetrahedron Letters",

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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.

N1 - Funding Information: Support was provided by the Fund for Scientific Research (FWO), Flanders and by the Research Fund of the University of Leuven (KU Leuven). N.M.M. is grateful to EMECW13 (Erasmus Mundus External Cooperation Window Lot 13 India) for obtaining a doctoral scholarship. V.A.P. is grateful to the EMECW (Triple I) for obtaining a doctoral scholarship. The authors thank Ir. B. Demarsin for valuable help with HRMS. Copyright: Copyright 2012 Elsevier B.V., All rights reserved.

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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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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