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
收藏
页码：4601 / 4607
页数：7
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