Synthesis of pyrazine acetals by the biased reaction of symmetric 2,5-bis(chloromethyl) or 2,3,5,6-tetrakis(chloromethyl) substituents on pyrazine ring with sodium alkoxides

Yusaku Eda, Yuta Odazaki, Akira Mizutani, Yoshio Ito, Toshio Kawato

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

2,5-Bis(chloromethyl)pyrazine reacted with sodium alkoxide to give unexpected 2-dialkoxymethyl-5-methylpyrazine along with normal substitution product, 2,5-bis(alkoxymethyl)pyrazine. The reaction of 2,3,5,6-tetrakis(chloromethyl)pyrazine with sodium alkoxide afforded similar results to yield 2,6-bis(dialkoxymethyl)-3,5-dimethylpyrazine along with other alkoxymethylpyrazines. The ratio of products depended on the solvent and alkoxide used. A general discussion of the mechanism of such a pyrazine acetal synthesis in the basic conditions is given.

Original languageEnglish
Pages (from-to)2519-2522
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number16
DOIs
Publication statusPublished - Apr 14 2008

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Pyrazines
Acetals
Sodium
Substitution reactions

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of pyrazine acetals by the biased reaction of symmetric 2,5-bis(chloromethyl) or 2,3,5,6-tetrakis(chloromethyl) substituents on pyrazine ring with sodium alkoxides. / Eda, Yusaku; Odazaki, Yuta; Mizutani, Akira; Ito, Yoshio; Kawato, Toshio.

In: Tetrahedron Letters, Vol. 49, No. 16, 14.04.2008, p. 2519-2522.

Research output: Contribution to journalArticle

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abstract = "2,5-Bis(chloromethyl)pyrazine reacted with sodium alkoxide to give unexpected 2-dialkoxymethyl-5-methylpyrazine along with normal substitution product, 2,5-bis(alkoxymethyl)pyrazine. The reaction of 2,3,5,6-tetrakis(chloromethyl)pyrazine with sodium alkoxide afforded similar results to yield 2,6-bis(dialkoxymethyl)-3,5-dimethylpyrazine along with other alkoxymethylpyrazines. The ratio of products depended on the solvent and alkoxide used. A general discussion of the mechanism of such a pyrazine acetal synthesis in the basic conditions is given.",
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AU - Eda, Yusaku

AU - Odazaki, Yuta

AU - Mizutani, Akira

AU - Ito, Yoshio

AU - Kawato, Toshio

PY - 2008/4/14

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AB - 2,5-Bis(chloromethyl)pyrazine reacted with sodium alkoxide to give unexpected 2-dialkoxymethyl-5-methylpyrazine along with normal substitution product, 2,5-bis(alkoxymethyl)pyrazine. The reaction of 2,3,5,6-tetrakis(chloromethyl)pyrazine with sodium alkoxide afforded similar results to yield 2,6-bis(dialkoxymethyl)-3,5-dimethylpyrazine along with other alkoxymethylpyrazines. The ratio of products depended on the solvent and alkoxide used. A general discussion of the mechanism of such a pyrazine acetal synthesis in the basic conditions is given.

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