Hétérocycles à fonction quinone. V. Réaction anormale de la butanedione avec la diamino-1,2 anthraquinone; structure cristalline de la naphto [2,3-f] quinoxalinedione-7,12 obtenue

Abstract

Butanedione reacts on heating with 1,2-diaminoanthraquinone to give, not the expected 2,3-dimethyl-naphtho[2,3-f]quinoxaline-7,12-dione 3, but 2-(2-hydroxy-2-methyl-3-oxobutyl)-3-methylnaphtho[2,3-f]quinoxaline-7,12-dione 4a whose structure was established by X-ray diffraction. This compound crystallizes in the triclinic [Formula: see text] space group with unit cell dimensions of a = 9.091 (1), b = 16.966 (4), c = 12.375 (3) Å; α = 100.75 (2), β = 101.83 (2), γ = 100.29 (2)°, V = 1789 Å3, Z = 4. The structure was resolved by the direct method and refined to R = 0.039 for 3027 independent reflections. The overall conformation of the molecule is essentially planar. The principal characteristic is the presence of two cyclic arrangements caused by intramolecular hydrogen bonding. 2,3-Dimethylnaphtho[2,3-f]quinoxaline-7,12-dione is the intermediate in this reaction.