A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives

被引：16

作者：

Babu, Kaki Raveendra ^{[1
]}

Khan, Faiz Ahmed ^{[1
]}

机构：

[1] Indian Inst Technol Hyderabad, Dept Chem, Yeddumailaram 502205, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 01期

关键词：

CARBONYLATIVE CYCLIZATION REACTIONS; C-H; CATALYZED ANNULATION; TANDEM REACTIONS; CHEMISTRY; ALKYNES; REARRANGEMENT; EFFICIENT; MECHANISM; STRATEGY;

D O I：

10.1039/c4ob01977f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient acid induced rearrangement of a tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl system leading to substituted indenones is reported. This domino reaction involves dehydration, olefin isomerization, ketal hydrolysis, [3,3]-sigmatropic rearrangement and dehydrohalogenation. The resultant vicinal dihalo olefin moiety in the efficiently generated indenone derivatives was utilized to transform into ninhydrin derivatives by employing Ru(III)-catalyzed oxidation.

引用

页码：299 / 308

页数：10

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