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

Ronald Grigg; H. Q.Nimal Gunaratne; Edward McNaghten

doi:10.1039/P19830000185

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

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

29 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 pK_a 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 language	English
Pages (from-to)	185-187
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/P19830000185
Publication status	Published - 1983

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Chemistry(all)

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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.",

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

Abstract

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