REACTION OF 4-CHLOROCOUMARIN WITH ORGANOMETALLIC REAGENTS - SYNTHESIS OF TRIALKYLBENZOPYRANS, 4-CHLOROBENZOPYRANS, 4-ALKYLCOUMARINS AND O-HYDROXYPHENYLPROP-2-YNYL ALCOHOLS

被引:10
作者
ALBEROLA, A [1 ]
CALVO, B [1 ]
ORTEGA, AG [1 ]
PEDROSA, R [1 ]
机构
[1] UNIV VALLADOLID,DEPT QUIM ORGAN,E-47005 VALLADOLID,SPAIN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 22期
关键词
D O I
10.1039/p19920003075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Chlorocoumarin has been shown to be a highly versatile starting material when treated with organometallic reagents. Thus, it has allowed the selective synthesis either directly, or through simple additional transformations, of 4-alkylcoumarins (with R2CuLi in Et2O, or PriMgBr in THF), 2-chloro-2-(o-hydroxyphenyl)allyl alcohols or their 4-chloro-2H-1-benzopyran derivatives (with RMgX in THF), 2-(o-hydroxyphenyl)prop-2-ynyl alcohols (when non-acid hydrolysis were used in the latter reactions) and 2,2,4-trialkyl-2H-1 -benzopyrans (when excess of RMgX or R3Al reagents were used).
引用
收藏
页码:3075 / 3080
页数:6
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