Synthesis of Chiral Polyhydroxylated Benzimidazoles by a Tandem Radical Fragmentation/Cyclization Reaction: A Straight Avenue to Fused Aromatic-Carbohydrate Hybrids
The synthesis of benzimidazole-fused iminosugars through a tandem β-fragmentation-intramolecular cyclization reaction is described. The use of the benzimidazole ring as the internal nucleophile and the use of phenyliodosophthalate (PhI(Phth)), a new metal-free and low toxic hypervalent iodine reagent, are the most remarkable novelties of this synthetic strategy. With this approach, we have demonstrated the usefulness of the fragmentation of anomeric alkoxyl radicals promoted by the PhI(Phth)/I system for the preparation of new compounds with potential interest for both medicinal and synthetic chemists.
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| Main Authors: | , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Published: |
ACS Publications
2018-12-27
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| Subjects: | Cyclization reaction, Synthesis, Radical fragmentation, Chiral polyhydroxylated benzimidazoles, |
| Online Access: | http://hdl.handle.net/10261/188341 http://dx.doi.org/10.13039/501100010198 http://dx.doi.org/10.13039/501100003339 |
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