387832-31-7Relevant academic research and scientific papers
Formation of pyridazinium salts by azo coupling of N-substituted 3-amino-1-phenylbut-2-en-1-ones and diazonium salts
Simunek, Petr,Peskova, Marketa,Bertolasi, Valerio,Lycka, Antonin,Machacek, Vladimir
, p. 5055 - 5063 (2004)
Treatment of 3-(2,4-dimethoxyphenylamino)- and 3-methylamino-1-phenylbut-2- en-1-ones with some benzenediazonium tetrafluoroborates gives, besides the usual azo coupling products [i.e., 3-(substituted imino)-1-phenylbutane-1,2-diones 2-(4-substituted phenylhydrazones) and 2-(4-methoxyphenyldiazenyl)-3- methylamino-1-phenylbut-2-en-1-one, respectively], the previously unreported 1,4,5,6-tetrasubstituted pyridazinium tetrafluoroborates. The pyridazinium salts have been identified by X-ray analysis and by their 1H, 13C, 15N, 11B and 19F NMR spectra. Their formation is most probably the result of nucleophilic attack on the carbonyl carbon by the nitrogen of the hydrazone group and subsequent dehydration. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
