Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke-Wilson Rearrangement

被引：30

作者：

Gopi, Elumalai ^{[1
]}

Namboothiri, Irishi N. N. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 03期

关键词：

ELECTROPHILIC CYCLIZATION; GEM-DIHALOCYCLOPROPANES; CYCLOPROPANATION; HETEROCYCLES; DERIVATIVES; FURANS;

D O I：

10.1021/jo3022988

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported.

引用

页码：910 / 919

页数：10

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