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

Aimin Song, Kit Lam

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The parallel solid-phase synthesis of a hydrophilic psoralen analogue, 2-arylamino-6H-pyrano[2,3-f]benzimidazole-6-ones (2-arylaminoimidazocoumarins), has been developed. The resin-bound 7-fluoro-4-methyl-6-nitro-2-oxo-2H-1- benzopyran-3-carboxylic acid underwent aromatic substitution with primary amines, followed by reduction of the nitro group with tin(II) chloride. The cyclization of the o-dianilino intermediates was accomplished with aryl isothiocyanates in the presence of 1,3-diisopropylcarbodiimide (DIC). The final products were released from the resin with trifluoroacetic acid (TFA) and obtained in high purity and good isolated yield. The 2-arylaminoimidazocoumarins exhibit interesting spectral properties.

Original languageEnglish (US)
Pages (from-to)8605-8612
Number of pages8
JournalTetrahedron
Volume60
Issue number39
DOIs
StatePublished - Sep 20 2004

Fingerprint

1,3-diisopropylcarbodiimide
Isothiocyanates
Ficusin
Trifluoroacetic Acid
Solid-Phase Synthesis Techniques
Cyclization
Amines
Resins
Tin
Chlorides
Substitution reactions
stannous chloride
benzimidazole
7-fluoro-4-methyl-6-nitro-2-oxo-2H-1-benzopyran-3-carboxylic acid
benzimidazol-2-one

Keywords

  • 2-Arylaminoimidazocoumarins
  • Photochemotherapy
  • Psoralen analogue
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Parallel solid-phase synthesis of 2-arylamino-6H-pyrano[2,3-f] benzimidazole-6-ones. / Song, Aimin; Lam, Kit.

In: Tetrahedron, Vol. 60, No. 39, 20.09.2004, p. 8605-8612.

Research output: Contribution to journalArticle

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N2 - The parallel solid-phase synthesis of a hydrophilic psoralen analogue, 2-arylamino-6H-pyrano[2,3-f]benzimidazole-6-ones (2-arylaminoimidazocoumarins), has been developed. The resin-bound 7-fluoro-4-methyl-6-nitro-2-oxo-2H-1- benzopyran-3-carboxylic acid underwent aromatic substitution with primary amines, followed by reduction of the nitro group with tin(II) chloride. The cyclization of the o-dianilino intermediates was accomplished with aryl isothiocyanates in the presence of 1,3-diisopropylcarbodiimide (DIC). The final products were released from the resin with trifluoroacetic acid (TFA) and obtained in high purity and good isolated yield. The 2-arylaminoimidazocoumarins exhibit interesting spectral properties.

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