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tert-Amino effect at a coumarin and a 2-quinolone system: Synthesis of 1,2 fused 5H-chromeno[4,3-b]pyridin-5-ones and a 6H-benzo[h][1,6]naphthyridin-5-one

✍ Scribed by Ivo C. Ivanov; Toma N. Glasnov; Ferdinand Belaj

Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 335 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450120

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✦ Synopsis

Abstract

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Some novel 1,2‐fused 5__H__‐chromeno[4,3‐b]pyridin‐5‐ones (5a,b) and a 6__H__‐benzo[h][1,6]naphthyridin‐5‐one (5c) have been synthesized starting from the 4‐chlorocoumarin‐3‐carbaldehyde (1a) or its N‐methyl‐2‐quinolone analogue (1b) via subsequent Knoevenagel condensation and ring closure reaction known as the ‘tert‐amino effect’. These are rare examples of the tert‐amino effect occurring at 2‐pyrone and 2‐pyridone ring. An unusual intramolecular redox reaction of the iminium ion 6, reported earlier, most probably follows analogous mechanism as the __tert‐__amino effect reactions leading to 5.

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