Nucleophilic substitution reaction at the 1-position of 1-hydroxytryptamine and -tryptophan derivatives

Abstract

金沢大学大学院自然科学研究科生理活性物質科学金沢大学大学院自然科学研究科生理活性物質科学金沢大学薬学部A novel nucleophilic substitution reaction at the 1-position of indole nucleus was discovered by reacting 1-hydroxytryptamine and -tryptophan derivatives with indoles in 85% formic acid yielding 1-(indol-3-yl)indoles. Their structures were determined by X-Ray crystallographic analysis and chemical correlations. An SN2 mechanism on the indole nitrogen (1-position) is proposed

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