A traceless approach for the parallel solid-phase synthesis of 2-(arylamino)quinazolinones

J Org Chem. 2002 Aug 9;67(16):5831-4. doi: 10.1021/jo020236g.

Abstract

A traceless approach for the parallel solid-phase synthesis of 2-arylamino-substituted quinazolinones is described. Acylation of MBHA resin with o-nitrobenzoic acid derivatives, followed by reduction of the nitro group with tin chloride, generated a resin-bound o-anilino derivative. Reaction of resin-bound o-anilino derivative with arylisothiocyanates yielded resin-bound thioureas, which reacted with amines in the present of Mukaiyama's reagent (2-chloro-1-methylpyridinium iodide) to afford resin-bound guanidines. Following intramolecular cyclization of the resin-bound guanidines during cleavage from the resin by HF/anisole (95/5) for 1.5 h at 0 degrees C, the desired products were obtained in good yield and purity.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Indicators and Reagents
  • Models, Molecular
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship

Substances

  • Indicators and Reagents
  • Quinazolines