Iodine(III)-Mediated Ring Contraction Reactions: Synthesis of Oxygen- and Nitrogen-Substituted Indanes

被引：2

作者：

Ahmad, Anees ^{[1
]}

Silva Junior, Luiz F. ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim, CP 26077, BR-05513970 Sao Paulo, SP, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2016年 / 27卷 / 10期

基金：

巴西圣保罗研究基金会;

关键词：

indane; hypervalent iodine; ring contraction; 1,2-dihydronaphthalenes; 3+2 ANNULATION; INHIBITORS; RECEPTOR; 1,2-DIHYDRONAPHTHALENES; ANALOGS; SULFONAMIDES; DERIVATIVES; ANTAGONISTS; ACTIVATION; COMPLEXES;

D O I：

10.5935/0103-5053.20160065

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of oxygen-and nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71% yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77% yield. The tosyl-protected substrate resulted only in addition products.

引用

页码：1820 / 1831

页数：12

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