Intramolecular aromatic nucleophilic substitution of the benzimidazole-activated nitro group.
A wide range of 2-(2-nitrophenyl)-1H-benzimidazoles undergo high-yielding intramolecular S(N)Ar of nitrite with N-pendant alkoxides under mild conditions (DMF, rt). When this operationally simple process is carried out at elevated temperatures in the presence of excess NaH, the initially formed S(N)Ar products are converted to the corresponding N-vinyl-substituted 2-(2-hydroxyphenyl)-1H-benzimidazoles via base-catalyzed isomerization. [reaction: see text]
Fekner
Tomasz
T
Department of Chemistry, The Ohio State University, 100 W 18th Avenue, Columbus, OH 43210, USA.
Gallucci
Judith
J
Chan
Michael K
MK
D001562:Benzimidazoles / Q000138:chemical synthesis*; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*
D001562:Benzimidazoles; D006576:Heterocyclic Compounds, 4 or More Rings; D009574:Nitro Compounds