Volume 20, Issue 22
Heterocyclic Compounds
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ChemInform Abstract: Synthesis of Substituted Tetrahydropyridines and m-Hydroxybenzoic Acids.

K. CLINCH

K. CLINCH

Dep. Chem., Univ. Edinburgh, Edinburgh EH9 3JJ, UK

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C. J. MARQUEZ

C. J. MARQUEZ

Dep. Chem., Univ. Edinburgh, Edinburgh EH9 3JJ, UK

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M. J. PARROTT

M. J. PARROTT

Dep. Chem., Univ. Edinburgh, Edinburgh EH9 3JJ, UK

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R. RAMAGE

R. RAMAGE

Dep. Chem., Univ. Edinburgh, Edinburgh EH9 3JJ, UK

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First published: May 30, 1989

Abstract

With the ultimate objective of designing acyclic pro-drugs of the areca and ergot types, a series of substituted tetrahydropyridines such as (VII) and/or (VIII) is synthesized via intramolecular 1,6-Michael addition of amines such as (VI).

ChemInform Abstract

With the ultimate objective of designing acyclic pro-drugs of the areca and ergot types, a series of substituted tetrahydropyridines such as (VII) and/or (VIII) is synthesized via intramolecular 1,6-Michael addition of amines such as (VI). The amines (VI), in turn, can be prepared starting from a Wittig reaction of the readily obtainable aldehydes (II) via the intermediates (III) and (IV). In addition, a new route to m-hydroxybenzoic acids such as (IX) is established by cyclization of hexadienoic acids such as (IV).

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