Sustainable Synthesis of 2‐Hydroxymethylbenzimidazoles using D‐Fructose as a C2 Synthon
- 22 September 2021
- journal article
- research article
- Published by Wiley in Chemistry – An Asian Journal
- Vol. 16 (22), 3754-3759
- https://doi.org/10.1002/asia.202100972
Abstract
D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2 phenylenediamines. The proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol %), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 oC for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product suggesting a new reaction pathway from D-fructose.Keywords
Funding Information
- Department of Chemistry, University of York
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