The diels-alder reaction witH O-2,3-Dimethylene-1,4-Naphtoquinone: a useful intermediate for the synthesis of b ring of anthracyclinones

Resumo

This work describes the attempt to use the diene ortho-2,3-dimetbylene-l ,4-naphthoquinone (3) in a Diels-Alder reaction with typical dienophiles. The intennediate 3 is useful for the synthesis ofthe anthracyclinone skeleton by a convergent route to the B ring. The reactions failed to gíve the desired Diels-Alder adduct in a good yield, but instead led to a spiro-dimer 9 which was recently described as a trypanocide agent. Among the by-products generated in these reactions it was possible to isolate and cbaracterize a new heterocyclic compound 13.

Descrição

Palavras-chave

Anthracyclinone, Dimethylenenaphthoquinone, Diels-alder reaction

Citação

FERREIRA, Vitor F. et al. The diels-alder reaction witH O-2,3-Dimethylene-1,4-Naphtoquinone: a useful intermediate for the synthesis of b ring of anthracyclinones. Journal of the Brazilian Chemical Society, Campinas, v. 7, n. 3, p. 169 - 172, 1996.