78893-12-6Relevant articles and documents
Electrochemical Synthesis of Heterocyclic Compounds. 17. Anodic Oxidation of Hydrazones in the Presence of Heteroaromatic and Schiff Bases
Gunic, Esmir,Tabakovic, Ibro
, p. 5081 - 5087 (2007/10/02)
Anodic oxidation of a series of hydrazones in the presence of heteroaromatic and Schiff bases were performed in acetonitrile-tetraethylammonium perchlorate electrolyte solution at platinum using controlled potentials.As a result of four-electron oxidation several s-triazolopyridinium perchlorates (1-9), s-triazoloquinolinium perchlorate (10), s-triazoloisoquinolinium perchlorate (11), and s-triazolobenzoquinolinium perchlorate (12) were obtained in yields ranging from 30percent to 90percent.As a result of two-electron oxidation of -p-nitrophenylhydrazine (A) in the presence of imidazole and 1,2,4-triazole the azo derivatives 13 and 14 were obtained with high yields.As a result of two-electron oxidation of hydrazone A in the presence of Schiff bases the new Schiff bases 15-20 were obtained in high yields.On the bases of the electroanalytical and preparative results it is concluded that the electrochemical oxidation of hydrazone A in the presence of heteroaromatic and Schiff bases occurs through the formation of cation B, which is attacked by base as a nucleophile.This excludes the possibility of annelation of the heteroaromatics through nitrilimine as an intermediate.
SYNTHESIS OF S-TRIAZOLOPYRIDINIUM SALTS BY ANODIC OXIDATION OF HYDRAZONES IN THE PRESENCE OF PYRIDINE
Tabakovic, Ibro,Crljenak, Senka
, p. 699 - 702 (2007/10/02)
The anodic oxidation of some aldehyde hydrazones in the presence of pyridine was investigated.From the reaction mixture derivatives of s-triazolopyridinium salts were isolated in 45-80percent yield and identified.The mechanism of these transformatio