One-step synthesis of 2,9-disubstituted phenanthrenes via Diels-Alder reactions using 1,4-disubstituted naphthalenes as dienophiles

被引：25
|
作者：
Paredes, E [1 ]
Biolatto, B [1 ]
Kneeteman, M [1 ]
Mancini, P [1 ]
机构：
[1] Univ Nacl Litoral, Fac Ingn Quim, Dept Quim, Area Quim Organ, RA-3000 Santa Fe, Argentina
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 26期
关键词：
Diels-Alder; dienophiles; phenanthrenes;
D O I：
10.1016/S0040-4039(02)00879-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The normal electron-demand Diels-Alder reaction between 1,4-disubstituted naphthalenes. nitro being one of these two groups. and 1-methoxy-3-trimethylsililoxy-1,3-butadiene gives hydroxyphenanthrene derivatives, the yields being enhanced by placement of more electron-withdrawing groups on the dienophilic system. The nitro group as substituent directs the cycloaddition, and its cis-extrusion as nitrous acid along with the loss of methanol from primary adducts leads to the expected aromatized products. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4601 / 4603
页数：3
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