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Synfacts 2006(1): 0025-0025
DOI: 10.1055/s-2005-921691
DOI: 10.1055/s-2005-921691
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Indolizine Derivatives by Electrocyclization
J. Kaloko Jr., A. Hayford*
East Carolina University, Greenville, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
16. Dezember 2005 (online)
Significance
A rapid and efficient synthesis of indolizine derivatives is presented. The silylated enyne pyridine and quinoline precursors, obtained by a Wittig-Sonogashira sequence, undergo an unexpected electrocyclic ring closure, which is triggered by a fluoride-mediated desilylation reaction under mild conditions. A plausible mechanism is proposed on the basis of analysis of deuterium labelling experiments.