SYNTHESIS OF HALOGEN DERIVATIVES OF N-ARYLAMINOCARBONYL-1,4-BENZOQUINONE MONOIMINES

Abstract

The hydrohalogenation of N-arylaminocarbonyl-1,4-benzoquinone monoimines is optimal method to obtain the halogenated derivatives. This method allows obtaining the pure products in high yield with a halogen atom in the aminophenol ring. The bromination of N-arylaminocarbonyl-1,4-benzoquinone monoimines and their reduced forms allows obtaining of individual products only in several cases. The bromination allows synthesizing of products with a halogen atom not only in the aminophenol ring, but in the aryl moiety too. As a result of the experiment we have found the optimal conditions to synthesis the N-arylaminocarbonyl-1,4-benzoquinone monoimine derivatives containing halogen atom. The bromination and hydrohalogenation products with one free ortho-position toward to the imine carbon atom of the quinoid ring can be used as synthons in the synthesis of heterocyclic compounds – 1,3-benzoxazole derivatives.

Keywords

• N-ариламінокарбоніл-1,4-бензохінонмоноіміни
• бромування
• гідрогалогенування
• окиснення