Reduction of different electron-poor N-heteroarylhydrazines in strong basic conditions was written by Unciti-Broceta, Asier;Pineda de las Infantas, Maria J.;Gallo, Miguel A.;Espinosa, Antonio. And the article was included in Chemistry – A European Journal in 2007.Electric Literature of C7H5N3 This article mentions the following:
The 1st application of the Wolff-Kishner reduction methodol. to electron-poor heteroaromatic compounds is reported. Hydrazino-containing heterocycles with hydrazone-type tautomery were reduced under basic conditions. This novel chem. was successfully applied to mono-dehalogenate a number of electron-poor heterocycles in a regioselective manner, e.g. 2,6-dichloropurine to 2-chloropurine. According to the exptl. results, this reductive process is a base-catalyzed reaction that takes only place in the presence of air, probably through an oxygen-assisted mechanism. As a consequence of the specific features of this kind of hydrazone/enehydrazine tautomers, the overall outcome of the process is the synthesis of a Shapiro-type reduction product by simply using a milder version of the Huang-Minlon methodol. The crystal and mol. structures of 2-propoxypyrido[2,3-b]pyrazine were determined by x-ray crystallog. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Electric Literature of C7H5N3).
Pyrido[2,3-b]pyrazine (cas: 322-46-3) belongs to pyrazine derivatives. Pyrazinesare six-membered aromatic heterocyclic organic compounds with two nitrogen atoms at 1,4-positions. Pyrazine is a weaker base (pKb = 13.4) than pyridine (pKb = 8.8), pyrimidine (pKb = 12.7). Pyrazines are chemical compounds (technically called “methoxypyrazines”) found in grape skin and stems that are responsible for many “green” flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.Electric Literature of C7H5N3