TY - JOUR
T1 - 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
AU - Eda, Yusaku
AU - Odazaki, Yuta
AU - Mizutani, Akira
AU - Ito, Yoshio N.
AU - Kawato, Toshio
N1 - Funding Information:
The present work was supported by a Grant-in-Aid for Priority Areas (417, No. 17029049) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan.
PY - 2008/4/14
Y1 - 2008/4/14
N2 - 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.
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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U2 - 10.1016/j.tetlet.2008.02.119
DO - 10.1016/j.tetlet.2008.02.119
M3 - Article
AN - SCOPUS:40849111241
SN - 0040-4039
VL - 49
SP - 2519
EP - 2522
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 16
ER -