Preparation of some p-amino quinone derivatives

Abstract

p-Quinones are a group of compounds which played a vital role in biological processes through their redox system in the respiratory cycles and blood stream. The chemistry of p-quinones including their preparations, reactions and different physicochemical properties were dealt with chapter one of this thesis. Twelve compounds of p-amino-quinone were prepared in this work: four were prepared from 1,4-benzoquinone: 2,5-dianilino-1,4-benzoquinone (Ia), 2,5-disulphamethoxazolyl-1,4-benzoquinone (Ib), 2,5-disulphadoxinyl-1,4-benzoquinone (Ic), 2,5-disulphanil amidyl-1,4-benzoquinone (Id); four were prepared from 2,3,5,6-tetrabromo-1,4-benzoquinone: 3,6-dibromo-2,5-dianilino-1,4-benzoquinone (IIa), 3,6-dibromo-2,5-disulphamethoxazolyl-1,4-benzoquinone (IIb), 3,6-dibromo-2,5-disulphadoxinyl-1,4-benzoquinone (IIc), 3,6-dibromo-2,5-disulphanilamidyl-1,4-benzoquinone (IId); four were prepared from 1,4-naphthoquinone: 2-anilino-1,4-naphthoquinone (IIIa), 2-sulphamethoxazolyl-1,4-naphthoquinone (IIIb), 2-sulphadoxinyl-1,4-naphthoquinone (IIIc) and 2-sulphanil amidyl-1,4-naphthoquinone (IIId). The compounds were prepared according to well established literature methods. They are selected based upon the calculated values of their physiochemical properties especially logP when correlated with the substituted groups. The identities of the prepared compounds were confirmed by infrared IR, ultraviolet-visible UV-VIS and proton-nuclear magnetic resonance 1H-NMR spectral analysis and chromatographic examination. Physiochemical properties, Mechanisms of the reactions and the appropriate retrosynthetic analysis were given and discussed in chapter three.