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Paper | Regular issue | Vol 53, No. 3, 2000, pp.585-598
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8771
Synthesis of 2H -Naphtho[2,3-b ]thiopyranoquinones and Density Functional Study for the Diels-Alder Reaction of a Benzothiopyranoquinone

Ricardo A. Tapia,* Miriam C. Garate, Jaime A. Valderrama, Fernando Zuloaga, Paul R. Jenkins, John Fawcett, and David R. Russell

*Facultad de Quimica, Pontificia Universidad Catolica de Chile. Casilla 306, Santiago 22, Chile


The synthesis of benzothiopyranoquinone (6) in three step from benzothiopyran (3) is described. Diels-Alder reaction of quinone (6) with 1,3-pentadiene (7), cyclopentadiene, 1-methoxy-1,3-cyclohexadiene (11) and 1-dimethylamino-1-aza-1,3-pentadiene (14) was studied. The Density Functional Theory was applied to explain the orientation of the cycloaddition reaction of quinone (6) with dienes (7), (11) and (14).