Novel approaches for the solid-phase synthesis of biheterocyclic dihydroimidazole analogues.
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.
Acharya
Achyuta N
AN
Torrey Pines Institute for Molecular Studies, 3550 General Atomics Court, San Diego, California 92121, USA.
Ostresh
John M
JM
Houghten
Richard A
RA
D000586:Amination; D000596:Amino Acids / Q000737:chemistry; D001562:Benzimidazoles / Q000138:chemical synthesis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D015195:Drug Design; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D007093:Imidazoles / Q000138:chemical synthesis*; D012117:Resins, Synthetic / Q000737:chemistry
D000596:Amino Acids; D001562:Benzimidazoles; D006574:Heterocyclic Compounds, 2-Ring; D007093:Imidazoles; D012117:Resins, Synthetic