Diels-Alder reactions of five-membered heterocycles containing one heteroatom

被引：30
|
作者：
Ding, Xiaoyuan [1 ]
Nguyen, Son T. [1 ]
Williams, John D. [1 ]
Peet, Norton P. [1 ]
机构：
[1] Microbiotix Inc, Dept Chem, Worcester, MA 01605 USA
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 51期
关键词：
Diels-Alder reactions; Dienes; Dienophiles; Acid-catalyzed reactions; SERIES; ROUTE;
D O I：
10.1016/j.tetlet.2014.10.114
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diels-Alder reactions of five-membered heterocycles containing one heteroatom with an N-arylmaleimide were studied. Cycloaddition of 2,5-dimethylfuran (4) with 2-(4-methylphenyl)maleimide (3) in toluene at 60 degrees C gave bicyclic adduct 5. Cycloadditions of 3 with 2,5-dimethylthiophene (11) and 1,2,5-trimethylpyrrole (14) were also studied. Interestingly, the bicyclic compound 5 cleanly rearranged, with loss of water, when treated with p-toluenesulfonic acid in toluene at 80 degrees C to give 4,7-dimethyl-2-p-tolylisoindoline-1, 3-dione (6). (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7002 / 7006
页数：5
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