Nucleophilic Substitution Reaction at the 1-Position of 1-Hydroxytryptamine and -tryptophan Derivatives

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.