86344-88-9Relevant academic research and scientific papers
Tetrazinodihetarenes: Synthesis and Properties of New Multistep "Weitz-Type" Redox Systems
Stumpf, Martin,Balli, Heinz
, p. 1049 - 1054 (2007/10/02)
The s-tetrazine derivatives 3a-d and 6 were obtained by electrophilic amination of N-heterocycles bearing a leaving group in α-position and subsequent condensation under basic conditions.The corresponding N-amino salts 2a-f, 5 and 7 could be isolated and characterised.Under the same conditions, it was not possible to obtain a corresponding tetrazine from 5 but the mesoionic hetarylium-N-imide 6 could be isolated.The structure of 11 was supported by X-ray structure determination of its hydrogen sulfate salt.The redox potentials of the new compounds were determined by cyclovoltammetric methods.The tetrazines easily form radical salts which show unusually high stability. - Key Words: s-Tetrazine derivatives / Redox systems, organic / Hetarylium-N-imides / Amination, electrophilic / Electrochemistry / Cyclovoltammetry
Chemistry of Thienopyridines. XXIX. The Reissert-Henze Reaction as a Route to Simple C-Substituents alpha to the Heteronitrogen Atom
Klemm, L. H.,Muchiri, Daniel R.
, p. 213 - 217 (2007/10/02)
Treatment of a thienopyridine N-oxide with benzoyl chloride and cyanide ion (Reissert-Henze reaction) was shown to produce the corresponding cyanothienopyridine (43-84 percent yield in three parent systems), wherein the cyano susbstituent occurs alpha to the heteronitrogen atom.In further transformations (in two systems) the cyano group was converted successively to carbamoyl (66-89 percent) and thiocarbamoyl (35-43 percent) functions.For 4-substituted thienopyridine 7-oxides, methyl and chloro substituents were retained on Reissert-Henze reaction, but the nitro group was replaced by Cl or H.Some new N-oxides and N-oxide complexes are reported.
