Abstract
A new method of 5-chloropyrazine-2-carbonitrile preparation in a regioselective fashion and the study of the coupling of the pyrazine ring with variously substituted benzenethiols are described. A radical-ionic mechanism of this coupling, carried out in the presence of a heterogeneous copper catalyst, has been proposed. The reactivity of the substituted chloropyrazines is correlated to the calculated values of electronic deficiency in positions C(6) or C(5) or C(3) of the pyrazine ring. This nucleophilic substitution provided a series of substituted phenylsulfanylpyrazine-2- carboxylic acid derivatives. The synthetic approach, analytical and spectroscopic data of all compounds are presented.
Keywords: halogenpyrazine, dehydration, synthesis
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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