A reinvestigation of the acid-promoted heterocyclization of 2-(2-oxo-2-arylethyl)malononitriles in the presence of amines

Carla Martins, Ana Eleutério, M. Carmo Carreiras, Abdelouahid Samadi, Elena Soriano, Rafael Léon, José Marco-Contelles

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The reinvestigation of the acid-promoted cyclization of 2-(2-oxo-2-arylethyl)malononitriles, in the presence of benzylamine or aniline, in ethanol or acetonitrile, has confirmed that this is a long-time reaction process for a low-yielding synthesis of 2-amino-5-arylfuran-3-carbonitriles (2), or 2-amino-5-aryl-1-phenyl-1H-pyrrole-3-carbonitriles (4), depending on the base used. However, the microwave-assisted synthesis of 2-amino-5-(4'- methoxyphenyl)furan-3(4)-(di)carbonitriles (2c and 3c) proceeds in shorter reaction times and higher yields than does the classical thermal heating protocol. In these reactions we have observed for the first time, and characterized by their spectroscopic data and X-ray analysis, the unexpected formation of 2-amino-5-aryl-3 (4)-(di)carbonitriles (3), whose formation has been rationalized by density functional theory (DFT) analysis of the proposed reaction mechanism.

Original languageEnglish
Pages (from-to)459-468
Number of pages10
JournalMolecular Diversity
Volume13
Issue number4
DOIs
Publication statusPublished - Nov 2009
Externally publishedYes

Keywords

  • 2-(2-Oxo-2-arylethyl)malononitriles
  • 2-Amino-5-aryl-1-phenyl-1H-pyrrole-3-carbonitriles
  • 2-Amino-5-arylfuran-3 (4)-(di)carbonitriles
  • 2-Amino-5-arylfuran-3-carbonitriles
  • DFT
  • MWI
  • Reaction mechanism

ASJC Scopus subject areas

  • Catalysis
  • Information Systems
  • Molecular Biology
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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