A GENERAL SYNTHETIC ROUTE TO ISOBENZOFURANS BEARING A FUNCTIONALIZED C-1 SUBSTITUENT

被引：27

作者：

MEEGALLA, SK ^{[1
]}

RODRIGO, R ^{[1
]}

机构：

[1] UNIV WATERLOO,GUELPH WATERLOO CTR GRAD WORK CHEM,DEPT CHEM,WATERLOO N2L 3G1,ONTARIO,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 05期

关键词：

D O I：

10.1021/jo00005a040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aromatic o-formyl acetals undergo base-catalyzed Claisen-Schmidt condensation with nitro compounds, ketones, methyl acetate, and acetonitrile to produce functionalized styrenes. Hydrolysis of the acetal and cyclization of the product in methanol provide methoxy phthalans 8 which are used to generate isobenzofurans bearing a functionalized substituent at C-1. The Diels-Alder reactions of these isobenzofurans with several dienophiles have been studied. Conjugated exo-methylene phthalans 20 have been isolated, and an unusual elimination of nitrous acid from nitroalkyl phthalans 8E and 8F has been observed.

引用

页码：1882 / 1888

页数：7

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