Tetrahedron

Polycyclic hydroxyquinones. XXVII. Tautomerism in 1, 4-Dihydroxy-9, 10-anthraquinone Monoimines. Cycloaddition Reactions of Their 1, 4-Anthraquinonoid …

F Fariña, MT Molina, P Noheda, MC Paredes

Index: Farina, Francisco; Molina, M. Teresa; Noheda, Pedro; Paredes, M. Carmen Tetrahedron, 1992 , vol. 48, # 39 p. 8437 - 8450

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Citation Number: 12

Abstract

1, 4-Dihydroxy-9, 10-anthraquinone monoimine and differently substituted derivatives thereof (6a-i) have been prepared by ammonolysis of the corresponding 1, 4-dihydroxy-9, 10-anthraquinones. 1H-and 13C-nmr studies show the existence of a rapid tautomeric equilibrium in quinone imines of type 6. Diels-Alder reaction with the 1, 4-anthraquinonoid tautomer of quinone monoimines 6a, e affords ABCD tetracyclic systems related to those ...