Observations on the pictet-spengler synthesis of 1, 2, 3, 4-tetrahydro-γ-carbolines

Ronald Grigg*, H. Q.Nimal Gunaratne, Edward McNaghten

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

The Pictet-Spengler cyclisation of the benzylideneimine of tryptophan methyl ester in xylene, contrary to literature reports, occurs extremely slowly, if at all, in the absence of acids. The cyclisation is Bronsted acid catalysed and the rate of cyclisation is related to the pKa of the Bronsted acid and its concentration. All the acid catalysts studied give essentially the same stereoisomeric mixture of tetrahydro-β-carbolines (cis:trans, ca. 1.2:1). The benzylideneimine of tryptamine smoothly cyclises under the same conditions.

Original languageEnglish
Pages (from-to)185-187
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - 1983

Bibliographical note

Copyright:
Copyright 2015 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

  • General Chemistry

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