Regioselective synthesis of pentacyclic polyheterocycles:: Sequential [3,3] sigmatropic rearrangement of 4-(4'-Aryloxybut-2'-ynyloxy)-1-phenyl-1,8-naphthyridin-2(1H)-ones

被引：3
|
作者：
Majumdar, Krishna C. [1 ]
Rafique-ul-Islam [1 ]
机构：
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2007年 / 44卷 / 04期
关键词：
D O I：
10.1002/jhet.5570440420
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A number of 4-aryloxymethyl-6-phenyl-2H-pyrano[3,2-c][1,8] naphthyridin-5(6H)-ones (4a-f) are regioselectively synthesized in 72-78% yield by the Claisen rearrangement of 4-(4'-aryloxybut-2'ynytoxy)-1-phenyl-1,8-naphthyridin-2(1H)-ones (3a-f) in refluxing chlorobenzene for 4-6 h. These products are then subjected to a second Claisen rearrangement catalyzed by anhydrous AlCl3 at room temperature for 2 h to give hitherto unreported pentacyclic heterocycles (5a-f) in 78-85% yield.
引用
收藏
页码：871 / 875
页数：5
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