A solid phase traceless synthesis of 2-arylaminobenzimidazoles

Viktor Krchňák, Jennifer Smith, Josef Vagner

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

A solid phase traceless synthesis of 2-arylaminobenzimidazoles in three combinatorial steps is reported that is based on acid lability of N-benzylanilines. MBHA resin was reacted with o-nitrobenzenes, the nitro group was reduced by tin(II) chloride, the resin-bound o-phenylene diamine was treated with isothiocyanates, and the resulting thiourea cyclized by carbodiimide. 2-Arylaminobenzimidazoles were further derivatized with alkyl halides. Target compounds were cleaved from the solid support by TFA or gaseous HF.

Original languageEnglish (US)
Pages (from-to)1627-1630
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number9
DOIs
StatePublished - Feb 26 2001
Externally publishedYes

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Nitrobenzenes
Isothiocyanates
Carbodiimides
Thiourea
Solid-Phase Synthesis Techniques
Diamines
Acids
Tin
Chlorides
Resins
benzylaniline
stannous chloride
4-methylbenzhydrylamine resin

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A solid phase traceless synthesis of 2-arylaminobenzimidazoles. / Krchňák, Viktor; Smith, Jennifer; Vagner, Josef.

In: Tetrahedron Letters, Vol. 42, No. 9, 26.02.2001, p. 1627-1630.

Research output: Contribution to journalArticle

Krchňák, Viktor ; Smith, Jennifer ; Vagner, Josef. / A solid phase traceless synthesis of 2-arylaminobenzimidazoles. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 9. pp. 1627-1630.
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