Tetrahedron

Syntheses of 1, 3-disubstituted N-oxy-β-carbolines by the Pictet-Spengler reactions of N-oxy-tryptophan and-tryptamine derivatives

PHH Hermkens, JH van Maarseveen, PLHM Cobben…

文献索引：Hermkens; Van Maarseveen; Cobben; Ottenheijm; Kruse; Scheeren Tetrahedron, 1990 , vol. 46, # 3 p. 833 - 846

全文：HTML全文

被引用次数: 32

摘要

A general and simple approach for the synthesis of N-hydroxy and N-alkoxytryptophan and tryptamine derivatives is presented. Key-intermediates are nitro compounds which are easily accessible from gramine (16) and RCH2N2. Reduction with Al-amalgam gave in high yields the corresponding hydroxylamines. The N-alkoxy derivatives are accesible by a regioselective O-alkylation of oxime 12 followed by a reduction with borane- ...