Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones

Xiaobing Wang, Seth Dixon, Mark J. Kurth, Kit Lam

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A traceless solid-phase route to 1,4-disubstituted-6-nitro-3,4-dihydro-1H- quinazolin-2-ones is described. N-Alloc-3-amino-3-(2-fluoro-5-nitrophenyl) propionic acid was tethered to Rink resin via its carboxylic group. The protected amine was coupled with an organic acid after Alloc-deprotection and the arylfluorine was displaced with a primary amine to generate a resin-bound aniline with two diversity points. The aniline was released via cleavage to produce the desired products in high yield and purity.

Original languageEnglish (US)
Pages (from-to)5361-5364
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number32
DOIs
StatePublished - Aug 8 2005

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Solid-Phase Synthesis Techniques
Amines
Resins
Organic acids
Acids
aniline
quinoline
propionic acid

Keywords

  • 3,4-Dihydro-1H-quinoline-2-one
  • Solid-phase synthesis
  • Traceless cleavage

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones. / Wang, Xiaobing; Dixon, Seth; Kurth, Mark J.; Lam, Kit.

In: Tetrahedron Letters, Vol. 46, No. 32, 08.08.2005, p. 5361-5364.

Research output: Contribution to journalArticle

Wang, Xiaobing ; Dixon, Seth ; Kurth, Mark J. ; Lam, Kit. / Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 32. pp. 5361-5364.
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