Tandem Diels−Alder Aromatization Reactions of Furans under Unconventional Reaction Conditions − Experimental and Theoretical Studies

✍ Scribed by José M. Fraile; José I. García; María A. Gómez; Antonio de la Hoz; José A. Mayoral; Andrés Moreno; Pilar Prieto; Luis Salvatella; Ester Vázquez

• Book ID: 101347220
• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 401 KB
• Volume: 2001
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200108)2001:15<2891::aid-ejoc2891>3.0.co;2-m

✦ Synopsis

Silica-supported Lewis acids are good catalysts for Diels-Alder reactions between furan and acrylonitrile and methyl acrylate at room temperature. When 2,5-dimethylfuran is used as the diene, yields of the Diels-Alder adducts with methyl acrylate are lower, due in part to the appearance of aromatization products. The use of microwave activation results in some cases in good yields of aromatic products and, as such, constitutes a good synthetic route to polysubstituted [a]