Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C Synthon.
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ID: 275493
2021
D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF .OEt (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH CN at 90 °C 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 C synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.
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| Authors | Raja, Dineshkumar;Philips, Abigail;Sundaramurthy, Devikala;Chandru Senadi, Gopal; |
| Journal | Chemistry, an Asian journal |
| Year | 2021 |
| DOI | 10.1002/asia.202100972 |
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