Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Benzimidazole N-Oxides. VI. Reaction of 3-Methoxy-1-methyl- and 1, 2-dimethyl-benzimidazolium Iodide with Various Nucleophiles
高橋 史郎加納 日出夫
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1966 年 14 巻 4 号 p. 375-385

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抄録
Reactions of 1-methyl- or 1, 2-dimethyl-3-methoxybenzimidazolium iodide (I or II) with various nucleophilic reagents (CN-, OH-, RO-, amines etc.) have been investigated. Most of these reagents reagents react with I to give the corresponding 2-substituted 1-methylbenzimidazole.The reaction of II with these reagents generally affords 1, 2-dimethylbenzimidazole (V) losing its methoxy group. Only with potassium cyanide, II undergoes substitution concurrently to give a mixture of 1, 2-dimethyl-6-benzimidazolecarbonitrile and V. The reaction mechanisms have been discussed as compared with those of Nalkoxypyridinium salt, and a possible zwitterion intermediate for the reaction of I is noted.
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© The Pharmaceutical Society of Japan
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