Synthesis 2005(1): 33-38  
DOI: 10.1055/s-2004-834916
PAPER
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 4 August 2004
Publication Date:
17 November 2004 (online)

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.

35

The stereochemistry of the oximes 7j-n was not determined.