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.
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页码：1882 / 1888
页数：7
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