Synthesis and structure of bifunctional N-alkylbenzimidazole phenylboronate derivatives

…, JAK Howard, LGF Patrick, CA Smethurst…

Index: Blatch, Alexandrea J.; Chetina, Olga V.; Howard, Judith A.K.; Patrick, Leonard G.F.; Smethurst, Christian A.; Whiting, Andrew Organic and Biomolecular Chemistry, 2006 , vol. 4, # 17 p. 3297 - 3302

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Citation Number: 24

Abstract

N-Methyl and Nn-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 ...