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Formation of Pyridazinium Salts by Azo Coupling of N-Substituted 3-Amino-1-phenylbut-2-en-1-ones and Diazonium Salts
Authors: Šimůnek Petr | Pešková Markéta | Bertolasi Valerio | Lyčka Antonín | Macháček Vladimír
Year: 2004
Type of publication: článek v odborném periodiku
Name of source: European Journal of Organic Chemistry
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 5055-5063
Titles:
Language Name Abstract Keywords
cze Tvorba pyridaziniových solí při azokopulaci N-substituovaných 3-Amino-1-fenylbut-2-en-1-onů a diazoniových solí Reakcí 3-(2,4-dimethoxyfenylamino)- and 3-methylamino-1-fenylbut-2-en-1-onů s některými benzenediazonium tetrafluoroboráty poskytuje kromě obvyklého produktu azokopulace tj., 3-(subst. imino)-1-fenylbutan-1,2-dionů a 2-(4-subs. fenylhydrazonů a 2-(4-methoxyfenyldiazenyl)-3-methylamino-1-fenylbut-2-en-1-on i doposud nepopsaný 1,4,5,6-tetrasubstituovaný pyridazinium tetrafluoroborát. Pyridaziniová sůl byla identifikována rentgenostrukturní analýzou a 1H, 13C, 15N, 11B a 19F NMR spektry.
eng Formation of Pyridazinium Salts by Azo Coupling of N-Substituted 3-Amino-1-phenylbut-2-en-1-ones and Diazonium Salts 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. Azo Coupling, Diazonium salts, Pyridazinium salts

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