ACYLAMINATION OF N-ARYLSULPHONYL-1,4-BENZOQUINONE MONOIMINES

Abstract

The acylamination of the N-substituted 1,4-benzoquinonimines is a simple method to enter the acylaminogroup into the quinoid ring. In this way, the final product with the unchangeable quinoid structure can be obtained in one stage. The acylamination was carried out as reaction of N-arylsulfonyl-1,4-benzoquinone monoimines and N-chloramide of 4-methylbenzoic acid. The starting N-arylsulfonyl-1,4-benzoquinone monoimines contained both donor and acceptor substituents in the quinoid ring. As a result, 2-(4-methylbenzoyl)amino-N-(4-methylphenyl) sulfonyl-1,4-benzoquinone monoimines were obtained. These monoimines are the products of substitution of the hydrogen atom of the free C=C bond of the quinoid ring of the starting quinone monoimine by the acylamino group. The nature of the substituent in the quinoid ring of the starting N-arylsulfonyl-1,4-benzoquinone monoimines does not influence on the reaction direction. The direction of the reaction depends on the first stage, and this reaction can be regarded as a 1,4-addition. The possibility of this reaction is determined by the steric factor. The same 2-(4-methylbenzoyl)amino-N-(4-methylphenyl)sulfonyl-1,4-benzoquinone monoimines were obtained in reaction of N-arylsulfonyl-1,4-benzoquinone monoamines with O-(4-methyl)benzoylbenzhydroxamic acid in the presence of potassium acetate. The first stage of this reaction is the formation of an anion of hydroxamic acid under the action of acetate anion. Thereafter, the anion is added to the free C=C bond of the quinoid ring. formation of the final product. The PASS program was used to analyze the potential biological activities of the synthetic compounds. All products were found to be inhibitory to the enzymes Glutamyl endopeptidase II, Insulysin, Hexokinase, and Omptin.