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

Yu, Y, Ostresh, JM, Houghten, RA. (2002). A traceless approach for the parallel solid-phase synthesis of 2-(arylamino)quinazolinones . JOURNAL OF ORGANIC CHEMISTRY, 67(16), 5831-5834. 10.1021/jo020236g

cited authors

  • Yu, Y; Ostresh, JM; Houghten, RA

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°C, the desired products were obtained in good yield and purity.

publication date

  • August 9, 2002

published in

Digital Object Identifier (DOI)

start page

  • 5831

end page

  • 5834

volume

  • 67

issue

  • 16