Facile solid-phase synthesis of 2,3-disubstituted 6H-pyrano[2,3-f]benzimidazole-6-ones

Aimin Song, Lucy Wu, Laura Ho, Kit Lam

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

We report herein the facile solid-phase synthesis of 2,3-disubstituted 6H-pyrano[2,3-f]benzimidazole-6-ones using 7-fluoro-4-methyl-6-nitro-2-oxo-2H-1-benzopyran-3-carboxylic acid as the scaffold. The fluorine of the resin-bound scaffold was first replaced by a primary amine. Reduction of the nitro group with tin(II) chloride afforded an o-dianilino intermediate that was treated with an aldehyde followed by the addition of 2,3-dichloro-5,6-dicyanoquinone (DDQ). 2,3-Disubstituted 6H-pyrano[2,3-f]benzimidazole-6-ones were obtained in high purity and good yield after cleavage.

Original languageEnglish (US)
Pages (from-to)4393-4399
Number of pages7
JournalTetrahedron
Volume62
Issue number18
DOIs
StatePublished - May 1 2006

Fingerprint

Solid-Phase Synthesis Techniques
Scaffolds
Fluorine
Tin
Aldehydes
Amines
Chlorides
Resins
benzimidazole
7-fluoro-4-methyl-6-nitro-2-oxo-2H-1-benzopyran-3-carboxylic acid
stannous chloride

Keywords

  • Combinatorial chemistry
  • Imidazocoumarins
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Facile solid-phase synthesis of 2,3-disubstituted 6H-pyrano[2,3-f]benzimidazole-6-ones. / Song, Aimin; Wu, Lucy; Ho, Laura; Lam, Kit.

In: Tetrahedron, Vol. 62, No. 18, 01.05.2006, p. 4393-4399.

Research output: Contribution to journalArticle

Song, Aimin ; Wu, Lucy ; Ho, Laura ; Lam, Kit. / Facile solid-phase synthesis of 2,3-disubstituted 6H-pyrano[2,3-f]benzimidazole-6-ones. In: Tetrahedron. 2006 ; Vol. 62, No. 18. pp. 4393-4399.
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