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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

✍ Scribed by Yusaku Eda; Yuta Odazaki; Akira Mizutani; Yoshio N. Ito; Toshio Kawato

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
116 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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## Abstract By heating 2‐chloromethyl‐3,‐5‐dimethyl‐4‐methoxypyridine **(1)** either neat or in solution methoxy group cleavage was achieved, followed by dimerisation to poorly soluble 6,12‐dihydro‐1,3,7,9‐tetramethyl‐5__H__,11__H__‐dipyrido[1,2‐a:1′,2′‐d]pyrazine‐2,8‐dione **(3)** in almost quanti