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The Formation of Tin-Nitrogen Bonds. V. The Selective 1-Substitution Reaction of Tetrazoles by the Reaction of 5-Substituted 2-(Tri- n -butylstannyl)tetrazoles with Methyl Iodide, Methyl p -Toluenesulfonate, Dimethyl Sulfate, and Ethyl Bromoacetate

1973; Oxford University Press; Volume: 46; Issue: 7 Linguagem: Inglês

10.1246/bcsj.46.2176

1348-0634

Tyûzô Isida, Tetsuo Akiyama, Kiyoshi Nabika, Keiiti Sisido, Sinpei Kozima,

Synthesis and Characterization of Heterocyclic Compounds

Abstract The selective 1-substitution reaction of tetrazole was developed by the treatment of 5-substituted 2-(tri-n-butylstannyl)tetrazoles with methyl iodide, methyl p-toluenesulfonate, dimethyl sulfate, or ethyl bromoacetate at room temperature. This selectivity was introduced by blocking the 2-nitrogen with the tri-n-butyltin group against the 2-substitution. In the case of 5-substituted 2-(trimethylstannyl)tetrazoles, a low selectivity was observed. The possible reaction pathways have been discussed.