Intramolecular Heterocyclization of O-Propargylated Aromatic Hydroxyaldehydes as an Expedient Route to Substituted Chromenopyridines under Metal-Free Conditions

Keskin S., BALCI M.

ORGANIC LETTERS, vol.17, no.4, pp.964-967, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 4
  • Publication Date: 2015
  • Doi Number: 10.1021/acs.orglett.5b00067
  • Journal Name: ORGANIC LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.964-967
  • Middle East Technical University Affiliated: Yes


A concise and regioselective approach to the synthesis of chromenopyridine and chromenopyridinone derivatives was developed. The synthetic strategy relies on the O-propargylation of aromatic hydroxyaldehydes followed by reaction with propargylamine. The intramolecular cycloaddition reaction between the alkyne and azadiene, which is formed as an intermediate, furnished the desired skeletons.