Solid-phase synthesis of 3-alkyl-2-arylamino-3,4-dihydroquinazolines

Aimin Song, Jan Mařík, Kit Lam

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

The solid-phase synthesis of 3-alkyl-2-arylamino-3,4-dihydroquinazolines using an N-Fmoc-β-amino-2-nitrobenzenepropanoic acid scaffold is described. The resin-bound scaffold was reductively alkylated with aldehydes or ketones after Fmoc deprotection, followed by reduction of the nitro group with tin(II) chloride. Subsequent cyclization of the 1,3-diamine intermediates with aryl isothiocyanates in the presence of 1,3-diisopropylcarbodiimide (DIC) afforded the desired products in high purity with moderate to good yield after trifluoroacetic acid (TFA) cleavage.

Original languageEnglish (US)
Pages (from-to)2727-2730
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number13
DOIs
StatePublished - Mar 22 2004

Keywords

  • β-Amino-2- nitrobenzenepropanoic acid
  • 3,4-Dihydroquinazolines
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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