The Journal of organic chemistry

Synthesis and Reactions of a Stable o-Quinoid 10-π-Electron System, Furo [3, 4-c] pyridine

TK Sarkar, SK Ghosh, TJ Chow

Index: Sarkar, Tarun K.; Ghosh, Sunil K.; Chow, Tahsin J. Journal of Organic Chemistry, 2000 , vol. 65, # 10 p. 3111 - 3115

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Citation Number: 15

Abstract

Methyl 4, 6-dichloro-3-(diethylamino) furo [3, 4-c] pyridine-1-carboxylate (6), an intermediate in the Hamaguchi-Ibata reaction involving the RhII-catalyzed intramolecular reaction of a diazo group with the carbonyl of an adjacent amido group, has been isolated and characterized. PM3 calculations reveal the heat of formation (Δ H f) of this remarkably stable molecule to be-77.7 kcal/mol. Compound 6 undergoes a facile Diels-Alder cycloaddition ...