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An improved synthesis of 5,6,7,8-tetrahydro-1,7-naphthyridine - a conformationally-restricted analog of 2-(3-pyridyl)ethylamine

✍ Scribed by Robert L. Dow; Steven R. Schneider

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
29 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The 5,6,7,8‐tetrahydro‐1,7‐naphthyridine (7) pharmacophore has the potential to serve as a confor‐mationally‐locked analog of the pharmacologically active 2‐(3‐pyridyl)ethylamine (1) core structure. This paper describes the synthesis of 5,6,7,8‐tetrahydro‐1,7‐naphthyridine (7) via a five‐step sequence, which affords a significant improvement over previously reported syntheses.

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## Abstract A new access to 5‐phenyl‐5,6,7,8‐tetrahydro‐1,6‐naphthyridines **25a‐28a** (n=1) and 5‐phenyl‐6,7,8,9‐tetrahydro‐5__H__‐pyrido[3,2‐__c__]azepines **25b‐28b** (n=2) has been developed by first preparing the functional pyridine moiety followed by intramolecular cyclization forming the par