A solid phase traceless synthesis of quinoxalinones

Viktor Krchňák, Lajos Szabo, Josef Vagner

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

A solid-phase traceless synthesis of quinoxalinones in three combinatorial steps is reported. An aldehyde functionalized polystyrene resin was reductively alkylated by amino acid methyl esters, and then the resin bound secondary amines were reacted with o-fluoronitrobenzenes. The resulting o-nitroanilines were reduced by tin chloride to the dianilines, which spontaneously cyclized. The amide nitrogen of the dihydroquinoxalinones obtained was alkylated by alkyl halides. After cleavage from the resin, the dihydroquinoxalinones were air oxidized to quinoxalinones. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)2835-2838
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number16
DOIs
StatePublished - Apr 15 2000
Externally publishedYes

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Solid-Phase Synthesis Techniques
Polystyrenes
Aldehydes
Amides
Amines
Esters
Nitrogen
Resins
Air
Amino Acids
stannous chloride
1-fluoro-2-nitrobenzene
2-nitroaniline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A solid phase traceless synthesis of quinoxalinones. / Krchňák, Viktor; Szabo, Lajos; Vagner, Josef.

In: Tetrahedron Letters, Vol. 41, No. 16, 15.04.2000, p. 2835-2838.

Research output: Contribution to journalArticle

Krchňák, Viktor ; Szabo, Lajos ; Vagner, Josef. / A solid phase traceless synthesis of quinoxalinones. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 16. pp. 2835-2838.
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