Synthesis of Methyl (E)-2-Nitromethylcinnamates Derived from Baylis-Hillman­ Acetates and Conversion into Several Coumarin Derivatives

Wan Pyo Hong; Kee-Jung Lee

doi:10.1055/s-2004-834916

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Synthesis of Methyl (E)-2-Nitromethylcinnamates Derived from Baylis-Hillman Acetates and Conversion into Several Coumarin Derivatives

Wan Pyo Hong, Kee-Jung Lee*
Organic Synthesis Laboratory, School of Chemical Engineering, Hanyang University, Seoul 133-791, South Korea
Fax: +82(2)22984101; e-Mail: leekj@hanyang.ac.kr;

Abstract

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Abstract

Fast and easy access to methyl (E)-2-nitromethylcinnamates, from the corresponding Baylis-Hillman acetates with NaNO₂ in DMF is described. Several ortho-chloro-2-nitromethylcinnamates undergo intramolecular aromatic substitution reaction followed by rearrangement to yield coumarin derivatives.

Key words

Baylis-Hillman reaction - sodium nitrite - methyl (E)-2-nitromethylcinnamates - nitronate anion - coumarin

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Synthesis of Methyl (E)-2-Nitromethylcinnamates Derived from Baylis-Hillman­ Acetates and Conversion into Several Coumarin Derivatives

Synthesis of Methyl (E)-2-Nitromethylcinnamates Derived from Baylis-Hillman Acetates and Conversion into Several Coumarin Derivatives