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Synthesis of 2,5-bis-arylpyridines by [4 + 2] cycloaddition of 1,4-bis aryl-2-aza-1,3-butadienes with electron-poor dienophiles

✍ Scribed by Jean-Laurent Paparin; Christophe Crévisy; René Grée; Loïc Toupet

Publisher: Journal of Heterocyclic Chemistry
Year: 2000
Tongue: English
Weight: 563 KB
Volume: 37
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570370230

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✦ Synopsis

Abstract

Tetrahydropyridines 4a, 4b, 4c and pyridines 7a, 7b, 7c, 9a, 9b, 9c were synthesized by a [4 + 2] cycloaddition between 1,4‐bis aryl‐2‐aza‐1,3‐butadienes and electron‐poor dienophiles. Dimeric cycloadducts 6a, 6b, 6c, were also isolated indicating a competition between the expected Hetero Diels‐Alder and a dimerization process.

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