The reaction of 2-amino-4 H-pyrans with N-bromosuccinimide

Abdelouahid Samadi, Daniel Silva, Mourad Chioua, Lourdes Infantes, Elena Soriano, José Marco-Contelles

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


Abstract: The reaction of racemic 2-amino-4H-pyrans, such as 3-amino-1-aryl-1H-benzo[f]chromene-2-carbonitriles, with N-bromosuccinimide (NBS), in CH2 Cl2, at room temperature, is a very quick, regio, stereoselective, and high yielding process, affording major racemic (1S,2S)-2-bromo-3-imino-benzo[f]chromene or racemic (1S,2S)-2-bromo-3-(bromoimino)-benzo[f]chromene derivatives, when using 1.0 or 2.2 equivalents of NBS, respectively. This reaction, extended to isomeric 2-amino-4-aryl-4H-benzo[h]chromene-3-carbonitriles, showed an unexpected reactivity, affording racemic (3S,4S)-3-bromo-2-(bromoimino)-benzo[h]chromene-3-carbonitriles or 2-oxo-2H-benzo[h]chromene-3-carbonitriles, when using 2.2 or 1.0 equivalents of NBS, respectively. The reaction of alkyl 6-amino-5-cyano-2-methyl-4H-pyran-3-carboxylates has yielded unstable racemic (3S,4S)-alkyl 3-bromo-2-(bromoimino)-3-cyano-6-methyl-3,4-dihydro-2H-pyran-5-carboxylates. The mechanism of these reactions has been investigated by computational methods.

Original languageEnglish
Pages (from-to)103-122
Number of pages20
JournalMolecular Diversity
Issue number1
Publication statusPublished - Jan 23 2015
Externally publishedYes


  • 2-Amino-4H-pyrans
  • DFT
  • N-Bromosuccinimide
  • NBS
  • 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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