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2-Nitrobenzothiophene and 3-Nitrobenzothiophene as Electrophiles in Polar Diels-Alder Reactions. Solvent Effects
1 , 2 , * 2
1  Área Química Orgánica- Departamento de Química- Facultad de Ingeniería Química, Universidad Nacional del Litoral. Santiago del Estero 2829. (3000) Santa Fe, Argentina. FAX: +54-342-4571162. *
2  Laboratorio Fester–IQAL (UNL-CONICET)– Facultad de Ingeniería Química – Santiago del Estero 2829, (3000), Santa Fe, Argentina.

Abstract: In this work the polar Diels-Alder reactions between 2- and 3-nitrobenzothiophenes derivatives and different dienes, such as 2-methyl-1,3-butadiene and 1-trimethylsilyloxy-1,3-butadiene are studied. Molecular solvent and protic ionic liquids are employed as reaction media. A very strong electron-acceptor group such as nitro group, push the electrophilic character of these heterocyclic compounds. Moreover, this substituent is easily extruded under thermal conditions make this reaction sequence a simple method of organic compound´s families with heteroatom rings preparation.
Keywords: nitrobenzothiophene, electrophile, Diels-Alder