Novel approaches for the solid-phase synthesis of biheterocyclic dihydroimidazole analogues Article

Acharya, AN, Ostresh, JM, Houghten, RA. (2002). Novel approaches for the solid-phase synthesis of biheterocyclic dihydroimidazole analogues . 4(3), 214-222. 10.1021/cc010067y

cited authors

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

abstract

  • The solid-phase syntheses of dihydroimidazolyl 2-alkylthiobenzimidazoles, dihydroimidazolyl 2-alkylsulfonylbenzimidazoles, dihydroimidazolyl dihydroquinoxalin-2,3-diones, and dihydroimidazolyl dihydrobenzimidazol-2-imines are described. Following reduction of a resin-bound amino acid amide, the primary amine of the resulting resin-bound diamine was N-acylated with 4-fluoro-3-nitrobenzoic acid. Treatment with POCl3 led to formation of a dihydroimidazole derivative via dehydrative cyclization. The resin-bound dihydroimidazole derivative was then used as the key starting material for the synthesis of the aforementioned biheterocycles. Following cleavage, the resulting compounds, obtained in moderate yield and good purity, were characterized by LC-MS and 1H NMR and 13C NMR spectroscopy.

publication date

  • May 1, 2002

Digital Object Identifier (DOI)

start page

  • 214

end page

  • 222

volume

  • 4

issue

  • 3