Michael Addition of N-Heteroaromatics to Vinylphosphonates and Synthesis of Phosphoryl Pyrrolizones by Cyclization of Michael Adducts

Dilek Isik Tasgin; Canan Unaleroglu

doi:10.1055/s-0032-1317894

Synthesis, Table of Contents

Synthesis 2013; 45(2): 193-198
DOI: 10.1055/s-0032-1317894

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Michael Addition of N-Heteroaromatics to Vinylphosphonates and Synthesis of Phosphoryl Pyrrolizones by Cyclization of Michael Adducts

Dilek Isik Tasgin

Hacettepe University, Department of Chemistry, 06800 Ankara, Turkey Fax: +90(312)2992163 Email: canan@hacettepe.edu.tr

,

Canan Unaleroglu*

Hacettepe University, Department of Chemistry, 06800 Ankara, Turkey Fax: +90(312)2992163 Email: canan@hacettepe.edu.tr

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Abstract

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Abstract

Novel phosphonate compounds were synthesized via Michael addition of N-heteroaromatic compounds to aryl- and alkyl-substituted vinylphosphonates using scandium triflate as the catalyst. Intramolecular cyclization reaction of the Michael adducts obtained gives novel (dimethoxyphosphoryl)pyrrolizin-3-ones in high yields as a single diastereomer.

Key words

phosphonates - pyrrolizinones - Michael addition - metal triflates - heteroaromatic compounds

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References

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