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Synthesis of 2H-chromeno[4,3-b]pyridine-2,5(1H)-diones and related heterocycles via the erlenmeyer-ploechl reaction

✍ Scribed by Ivo Christov Ivanov; Toma Nikolaev Glasnov; Dieter Heber

Publisher: Journal of Heterocyclic Chemistry
Year: 2005
Tongue: English
Weight: 94 KB
Volume: 42
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570420517

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✦ Synopsis

Abstract

1,2‐Dihydro‐5__H__‐[1]benzopyrano[4,3‐b]pyridine‐2,5‐diones 4a‐j were synthesized from 4‐alkylamino‐coumarin‐3‐carbaldehydes 1 and 5(4__H__)‐oxazolinones (azalactones) derived from N‐acetylglycine (2a) and hippuric acid (2b). The intermediates 3 (3j isolated only) underwent spontaneous recyclization via opening of the azalactone and successive formation of the fused 2‐pyridones 4. Attempts to synthesize the selected 2__H__‐chromeno[3,4‐f]‐1,7‐naphthyridine 6 by Vilsmeier reaction of 4e failed. Instead, N‐deacetylation took place, followed by formylation of the amino group to the formamidine 7a. In addition, pyranopyridine 9a was obtained by condensation of the 3‐formyl‐2‐pyridone 8 with the azalactone derived from 2a and acetic anhydride.

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