Synthesis 2015; 47(16): 2431-2438
DOI: 10.1055/s-0034-1380436
special topic
© Georg Thieme Verlag Stuttgart · New York

Enol-Ugi Reaction of Hydroxycoumarins: Straightforward Synthesis of Amino Acid Derived Coumarin Enamines

Ana G. Neo*
Laboratory of Bioorganic Chemistry & Membrane Biophysics, School of Veterinary Sciences, University of Extremadura, 10071 Cáceres, Spain   Email: cfernan@unex.es   Email: aneo@unex.es
,
Teresa G. Castellano
Laboratory of Bioorganic Chemistry & Membrane Biophysics, School of Veterinary Sciences, University of Extremadura, 10071 Cáceres, Spain   Email: cfernan@unex.es   Email: aneo@unex.es
,
Carlos F. Marcos*
Laboratory of Bioorganic Chemistry & Membrane Biophysics, School of Veterinary Sciences, University of Extremadura, 10071 Cáceres, Spain   Email: cfernan@unex.es   Email: aneo@unex.es
› Author Affiliations
Further Information

Publication History

Received: 21 April 2015

Accepted after revision: 24 May 2015

Publication Date:
25 June 2015 (online)

Abstract

Hydroxycoumarins containing electron-withdrawing groups have been successfully used as acidic components in Ugi-type multicomponent condensations with imines and isocyanides. The reaction takes place smoothly at room temperature, with no need of catalysis, affording 3- and 4-coumarin enamines in a highly convergent manner. Key to this transformation is the conjugate addition-β-elimination rearrangement on the primary adduct, irreversibly leading to the final product.

Supporting Information

 
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