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

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Tasgin D. I., ÜNALEROĞLU C.

SYNTHESIS-STUTTGART, vol.45, no.2, pp.193-198, 2013 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 45 Issue: 2
• Publication Date: 2013
• Doi Number: 10.1055/s-0032-1317894
• Journal Name: SYNTHESIS-STUTTGART
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.193-198
• Keywords: phosphonates, pyrrolizinones, Michael addition, metal triflates, heteroaromatic compounds, CYCLOPENTANE ANNULATED COMPOUNDS, EFFICIENT SYNTHESIS, REGIOSELECTIVE ALKYLATION, BIOLOGICAL-ACTIVITY, CONJUGATE ADDITION, PYRROLES, PHOSPHONATES, CONDENSATION, DERIVATIVES, PRODUCTS
• Hacettepe University Affiliated: Yes

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.