Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation

Yeon Ho Cho, Chun Young Lee, Cheol-Hong Cheon

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Highly efficient synthesis of benzofused heteroaromatic compounds via aerobic oxidation catalyzed by cyanide anion has been developed. The Schiff bases derived from 2-aminophenol and aldehydes provided the corresponding benzoxazoles in high yields in the presence of a catalytic amount of cyanide in an open flask under ambient conditions without the use of any external metal co-oxidants and bases. Furthermore, we have developed a catalytic sequential one-step protocol for the synthesis of benzoxazoles by adding a catalytic amount of NaCN to Schiff bases generated in situ from 2-aminophenol and aldehydes without the isolation of imine intermediates. This one-pot protocol was further extended to the synthesis of benzothiazoles from 2-aminothiophenol and aldehydes. A variety of aldehydes could be applied to this sequential one-pot protocol and the desired benzofused azole products were obtained in high yields.

Original languageEnglish
Pages (from-to)6565-6573
Number of pages9
JournalTetrahedron
Volume69
Issue number32
DOIs
Publication statusPublished - 2013 Aug 12

Fingerprint

Cyanides
Aldehydes
Benzoxazoles
Oxidation
Catalysts
Schiff Bases
Benzothiazoles
Azoles
Imines
Oxidants
Anions
Metals
2-aminophenol

Keywords

  • Aerobic oxidation
  • Benzothiazoles
  • Benzoxazoles
  • Cyanide
  • One-pot reaction

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation. / Cho, Yeon Ho; Lee, Chun Young; Cheon, Cheol-Hong.

In: Tetrahedron, Vol. 69, No. 32, 12.08.2013, p. 6565-6573.

Research output: Contribution to journalArticle

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