Efficient one-pot synthesis of tryptamines and tryptamine homologues by amination of chloroalkynes

Vivek Khedkar, Annegret Tillack, Manfred Michalik, Matthias Beller

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105 Scopus citations

Abstract

A new method was developed for the one-pot synthesis of substituted 3-(2-aminoethyl)- and 3-(3-aminopropyl)indoles from commercially available aryl hydrazines and chloroalkylalkynes. Various tryptamine derivatives were prepared directly in good yield with excellent regioselectivity. The method involves a new domino reaction sequence consisting of a titanium-catalyzed amination of the chloroalkylalkyne, [3+3]-rearrangement of the resulting aryl hydrazone, and nucleophilic substitution of the chloride by ammonia.

Original languageEnglish
Pages (from-to)3123-3126
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number15
DOIs
StatePublished - 5 Apr 2004
Externally publishedYes

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