Synthesis and structure of bifunctional N-alkylbenzimidazole phenylboronate derivatives.
N-Methyl and N-n-butyl-2-(2-boronophenyl)benzimidazoles are accessed from the corresponding mono-N-alkyl-ortho-phenylenediamines, either using a polyphosphoric acid-mediated cyclisation with ortho-bromobenzoic acid, or preferably using an Oxone-mediated cyclisation of the corresponding aldehyde, followed by a lithium-exchange and borylation sequence. The resulting boronic acids show unusual physical and chemical properties, as shown by 11B NMR and X-ray crystallography.
Blatch
Alexandrea J
AJ
Department of Chemistry, Durham University, Science Laboratories, South Road, Durham, UKDH1 3LE.
Chetina
Olga V
OV
Howard
Judith A K
JA
Patrick
Leonard G F
LG
Smethurst
Christian A
CA
Whiting
Andrew
A
D000478:Alkylation; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation
D001562:Benzimidazoles; D001897:Boronic Acids; D007202:Indicators and Reagents; C010686:benzeneboronic acid