Novel Regioselective Preparation of 5-Chloropyrazine-2-Carbonitrile from Pyrazine-2-Carboxamide and Coupling Study of Substituted Phenylsulfanylpyrazine- 2-Carboxylic Acid Derivatives

Title: Novel Regioselective Preparation of 5-Chloropyrazine-2-Carbonitrile from Pyrazine-2-Carboxamide and Coupling Study of Substituted Phenylsulfanylpyrazine- 2-Carboxylic Acid Derivatives

Volume: 9 Issue: 1

Author(s): Josef Jampilek, Martin Dolezal, Jiri Kunes, Dalibor Satinsky and Ivan Raich

Affiliation:

Keywords: halogenpyrazine, dehydration, synthesis

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.

Cite this article as:

Jampilek Josef, Dolezal Martin, Kunes Jiri, Satinsky Dalibor and Raich Ivan, Novel Regioselective Preparation of 5-Chloropyrazine-2-Carbonitrile from Pyrazine-2-Carboxamide and Coupling Study of Substituted Phenylsulfanylpyrazine- 2-Carboxylic Acid Derivatives, Current Organic Chemistry 2005; 9 (1) . https://dx.doi.org/10.2174/1385272053369312