Title:Ultrasound-assisted Synthesis of β-(N-arylamino)acrylates Derivatives, Key Intermediates of Biopotent Compounds
Volume: 22
Issue: 1
Author(s): Gabriel de Oliveira Costa, Victor Facchinetti, Gabriel Oliveira Guimarães Fernandes, Alexandra Mitidieri Bastos Mol Pimentel, Claudia Regina Brandão Gomes, James Lewis Wardell, Solange Maria Silva Wardell and Marcus Vinicius Nora De Souza*
Affiliation:
- Departamento de Síntese de Fármacos e Bioativos, Farmanguinhos/Fiocruz, R. Sizenando Nabuco, 100, Manguinhos,
21041-250, Rio de Janeiro, RJ, Brazil
Keywords:
β-anilineacrylates, sonochemistry, synthesis, multigram, building-blocks, gould-jacobs reaction.
Abstract: β-(N-arylamino)acrylates are building blocks of great industrial interest as they allow the
obtention of a variety of heterocyclic substances, such as quinoline and pyridone derivatives.
Therefore, the development of new methodologies for the synthesis of these substances is still of
interest. In this work, fourteen β-(N-arylamino)acrylates were synthesized in a multigram scale from
the reaction of mono- and di-substituted anilines with diethyl ethoxymethylenemalonate by
sonochemistry (US) and the results compared to those obtained by conventional heating. The use of
the US brought many benefits to these syntheses, including faster reactions and increased yields. The
crystal structure of diethyl 2-(((2-chloro-5-nitrophenyl)amino)methylene)malonate is also reported.
