Solid-phase parallel synthesis of substituted dihydroimidazolyl dihydrobenzimidazol-2-ones Article

Acharya, AN, Ostresh, JM, Houghten, RA. (2002). Solid-phase parallel synthesis of substituted dihydroimidazolyl dihydrobenzimidazol-2-ones . TETRAHEDRON, 58(11), 2095-2100. 10.1016/S0040-4020(02)00104-7

cited authors

  • Acharya, AN; Ostresh, JM; Houghten, RA

authors

abstract

  • The solid-phase synthesis of substituted (4,5-dihydro-1H-imidazole-2-yl)-1,3-dihydro-2H-benzimidazol-2-ones is described. Following the amide reduction of a resin-bound (MBHA resin) amino acid, the primary amine was selectively acylated with 4-fluoro-3-nitrobenzoic acid. Treatment with POCl3, displacement of the fluoro group, and reduction of the nitro group generated an o-dianiline. Cyclization with 1,1-carbonyldiimidazole resulted in a benzimidazolone analogue, which was subsequently N-alkylated with an alkyl halide. The compounds were cleaved from the solid-support using anhydrous HF and characterized by LC-MS and 1H and 13C NMR spectroscopy. © 2002 Elsevier Science Ltd. All rights reserved.

publication date

  • March 11, 2002

published in

Digital Object Identifier (DOI)

start page

  • 2095

end page

  • 2100

volume

  • 58

issue

  • 11