Abstract
Convenient methods for the synthesis of quinoxaline derivatives with the use of nucleophilic aromatic substitution of hydrogen in heteroaromatic part of molecule in conditions of the acid catalysis were elaborated. The reactions of substitution of fluorine with amines in aromatic ring of 6,7-difluoroquinoxaline with the formation of monofluoro derivatives were studied.
Highlights
Among derivatives of quinoxaline, compounds possessing various types of biological activities were found [1,2,3,4]
Quinoxalines are known to be applied as effective electroluminescent materials, dyes [7], organic semiconductors [8], building-blocks in the synthesis of anionic receptors [9] and cavitands [10, 11]
We succeeded in synthesizing various products of monosubstitution of quinoxaline under the conditions of acid catalysis
Summary
Compounds possessing various types of biological activities were found [1,2,3,4]. We consider reactions of quinoxalines with C-nucleophiles mediated by proton quaternary salt formation in conditions of acidic catalysis or by anions in activation of C-nucleophiles by bases. The reactions of hydrogen substitution by the methodology of the SNH-functionalization of C-H bonds are the most promising way for the preparation of derivatives, functionalized in heterocyclic moiety of quinoxaline [13]. Fluorine is the most promising atom in the reactions of nucleophilic substitution from the point of view of mobility. Quinoxaline hydrochloride on heating with N,N-dimethylaniline in the presence of sulfur affords the pro duct of substitution of the hydrogen [16]. This work is continuation of studies [13] on using methodologies of aromatic nucleophilic substitution of hydrogen and fluorine to obtain biologically active compounds
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