Synthesis of 3,3-dimethoxy-2-aryl-2,3-dihydro-1-oxa-cyclopenta[l]phenanthren-2-ols and their conversion to 2(3H)- and 3(2H)-furanones

被引：6

作者：

Jacob, AM ^{[1
]}

Thumpakkara, RK ^{[1
]}

Prathapan, S ^{[1
]}

Jose, B ^{[1
]}

机构：

[1] Cochin Univ Sci & Technol, Dept Appl Chem, Cochin 682022, Kerala, India

来源：

TETRAHEDRON | 2005年 / 61卷 / 19期

关键词：

furanol; furanone; phenanthrenequinone; rearrangement;

D O I：

10.1016/j.tet.2005.03.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of new 3,3-dimethoxy-2-aryl-2,3-dihydro-1-oxacyclopenta[I]phenanthren-2-ols were synthesized by the base-catalyzed reaction between phenanthrenequinone and 4-substituted acetophenones in methanol. These furanols are unstable and are easily converted to stable 3-methoxy-3-aryl-3H-1-oxacyclopenta[I]phenathren-2-ones in excellent yields. The furanols are converted to 2-aryl-1-oxacyclopenta[I]phenanthren-3-ones on treatment with acids. Plausible mechanisms for some of these new transformations are proposed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4601 / 4607

页数：7

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