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

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卷:55

Article

Ding, Xiaoyuan¹  Nguyen, Son T.¹  Williams, John D.¹  Peet, Norton P.¹ 

[1] Microbiotix Inc, Dept Chem, Worcester, MA 01605 USA

关键词: Diels-Alder reactions;    Dienes;    Dienophiles;    Acid-catalyzed reactions;   

DOI  :  10.1016/j.tetlet.2014.10.114

来源: Elsevier

【 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.

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