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Synlett 2001; 2001(6): 0753-0756
DOI: 10.1055/s-2001-14580
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Synergy between Heterogeneous Catalysis and Microwave Irradiation in an Efficient One-Pot Synthesis of Benzene Derivatives via Ring-Opening of Diels-Alder Cycloadducts of Substituted Furans

Antonio de la Hoz* , Angel Díaz-Ortiz, José María Fraile, María Victoria Gómez, José Antonio Mayoral, Andrés Moreno, Alfonso Saiz, Ester Vázquez
  • *Facultad de Química, Universidad de Castilla-La Mancha, Campus Universitario, 13071 Ciudad Real, Spain; Fax + 39 9 26 29 53 18; E-mail: adlh@qino-cr.uclm.es
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Publication Date:
31 December 2001 (online)

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The use of silica-supported Lewis acids as catalysts under microwave irradiation promotes regiospecific opening of the 7-oxa bridge of Diels-Alder cycloadducts, producing the corresponding arenes in a single step. This rapid and efficient procedure permits the synthesis of 1,2-, 1,2,4- and 1,2,3,4-substituted benzenes by reaction of 2,5-dimethylfuran (1), 2-methoxyfuran (2) and 2-ethylfuran (3) with dienophiles such as acrylonitrile, methyl acrylate, N-methylmaleimide and fumaronitrile.

furans - Diels-Alder reactions - heterogeneous catalysis - microwaves - arenes

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