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

页码：4601 / 4603

页数：3

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