Synthesis of Chiral Polyhydroxylated Benzimidazoles by a Tandem Radical Fragmentation/Cyclization Reaction: A Straight Avenue to Fused Aromatic-Carbohydrate Hybrids

被引：10

作者：

Andre-Joyaux, Emy ^{[1
]}

Santana, Andres G. ^{[1
]}

Gonzalez, Concepcion C. ^{[1
]}

机构：

[1] CSIC, Inst Prod Nat & Agrobiol, Ave Astrofis Francisco Snchez 3, Tenerife 38206, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 02期

关键词：

INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION; ANOMERIC ALKOXYL RADICALS; CLICK CHEMISTRY; ACID; GLYCOSIDES; OXIDATION; ALCOHOLS;

D O I：

10.1021/acs.joc.8b01988

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of benzimidazole-fused iminosugars through a tandem beta-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-2 system for the preparation of new compounds with potential interest for both medicinal and synthetic chemists.

引用

页码：506 / 515

页数：10

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