Regioselective double Boekelheide reaction: First synthesis of 3,6-dialkylpyrazine-2,5-dicarboxaldehydes from dl-alanine

Sajal Kumar Das; Joseph Frey

doi:10.1016/j.tetlet.2012.05.057

Regioselective double Boekelheide reaction: First synthesis of 3,6-dialkylpyrazine-2,5-dicarboxaldehydes from dl-alanine

Sajal Kumar Das, Joseph Frey

Department of Chemistry

Bar-Ilan University

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

10 Scopus citations

Abstract

Pyrazine-2,5-dicarboxaldehyde was synthesized on a multi-gram scale by MnO ₂ oxidation of 2,5-bis(hydroxymethyl)pyrazine, which in turn was obtained from 2,5-dimethylpyrazine employing double Boekelheide reaction as a key step as reported previously. This reaction was subsequently utilized in a regioselective fashion as a key step to synthesize efficiently, for the first time, 3,6-di(long-chain)alkylpyrazine-2,5-dicarboxaldehydes starting from dl-alanine. These monomers are certain to have importance as electron deficient and chemically versatile components for new materials development.

Original language	English
Pages (from-to)	3869-3872
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2012.05.057
State	Published - 25 Jul 2012

Bibliographical note

Funding Information:
This work was supported by the Israel Science Foundation Grant No. 1019/07 , and the Bar Ilan Institute for Nanotechnology and Advanced Materials to whom we are indebted.

Funding

This work was supported by the Israel Science Foundation Grant No. 1019/07 , and the Bar Ilan Institute for Nanotechnology and Advanced Materials to whom we are indebted.

Funders	Funder number
Bar Ilan Institute for Nanotechnology and Advanced Materials
Israel Science Foundation	1019/07

Keywords

Aromatic dialdehydes
Boekelheide reaction
Conjugated systems
Pyrazine dialdehydes
Regioselective

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title = "Regioselective double Boekelheide reaction: First synthesis of 3,6-dialkylpyrazine-2,5-dicarboxaldehydes from dl-alanine",

abstract = "Pyrazine-2,5-dicarboxaldehyde was synthesized on a multi-gram scale by MnO 2 oxidation of 2,5-bis(hydroxymethyl)pyrazine, which in turn was obtained from 2,5-dimethylpyrazine employing double Boekelheide reaction as a key step as reported previously. This reaction was subsequently utilized in a regioselective fashion as a key step to synthesize efficiently, for the first time, 3,6-di(long-chain)alkylpyrazine-2,5-dicarboxaldehydes starting from dl-alanine. These monomers are certain to have importance as electron deficient and chemically versatile components for new materials development.",

keywords = "Aromatic dialdehydes, Boekelheide reaction, Conjugated systems, Pyrazine dialdehydes, Regioselective",

author = "Das, {Sajal Kumar} and Joseph Frey",

note = "Funding Information: This work was supported by the Israel Science Foundation Grant No. 1019/07 , and the Bar Ilan Institute for Nanotechnology and Advanced Materials to whom we are indebted. ",

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doi = "10.1016/j.tetlet.2012.05.057",

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AU - Frey, Joseph

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AB - Pyrazine-2,5-dicarboxaldehyde was synthesized on a multi-gram scale by MnO 2 oxidation of 2,5-bis(hydroxymethyl)pyrazine, which in turn was obtained from 2,5-dimethylpyrazine employing double Boekelheide reaction as a key step as reported previously. This reaction was subsequently utilized in a regioselective fashion as a key step to synthesize efficiently, for the first time, 3,6-di(long-chain)alkylpyrazine-2,5-dicarboxaldehydes starting from dl-alanine. These monomers are certain to have importance as electron deficient and chemically versatile components for new materials development.

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KW - Conjugated systems

KW - Pyrazine dialdehydes

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Regioselective double Boekelheide reaction: First synthesis of 3,6-dialkylpyrazine-2,5-dicarboxaldehydes from dl-alanine

Abstract

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Keywords

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