Et3N-Induced Demethylation−Annulation of 3-Alkynyl-4-methoxy-2-pyridones and Structurally Related Compounds in the Synthesis of Furan-Fused Heterocycles

Various 3-iodo-4-methoxypyridin-2-ones and related pyrone and coumarin derivatives have been demonstrated as readily available precursors of 2-substituted furan-fused heterocycles by means of in situ sequential Sonogashira-acetylide coupling, dealkylation, and regioselective furan annulation reactio...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2008-11, Vol.73 (21), p.8619-8622
Hauptverfasser:	Conreaux, David, Belot, Sébastien, Desbordes, Philippe, Monteiro, Nuno, Balme, Geneviève
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Coumarins Ethylamines Exact sciences and technology Furans - chemistry Heterocyclic compounds Heterocyclic Compounds - chemistry Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties Pyridones - chemistry Pyrones
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	Various 3-iodo-4-methoxypyridin-2-ones and related pyrone and coumarin derivatives have been demonstrated as readily available precursors of 2-substituted furan-fused heterocycles by means of in situ sequential Sonogashira-acetylide coupling, dealkylation, and regioselective furan annulation reactions. A Et3N-induced SN2 process has been established that accounts for the dealkylation process.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo8014038