期刊
TETRAHEDRON LETTERS
卷 55, 期 51, 页码 7002-7006出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.10.114
关键词
Diels-Alder reactions; Dienes; Dienophiles; Acid-catalyzed reactions
资金
- DHHS/NIH Grant from the National Institute of Allergy and Infectious Diseases (NIAID) NIH - United States [R43 AI-068185]
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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