Formation of Pyridazinium Salts by Azo Coupling of N-Substituted 3-Amino-1-phenylbut-2-en-1-ones and Diazonium Salts

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F04%3A00001970" target="_blank" >RIV/00216275:25310/04:00001970 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Formation of Pyridazinium Salts by Azo Coupling of N-Substituted 3-Amino-1-phenylbut-2-en-1-ones and Diazonium Salts

Original language description

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.

Czech name

Tvorba pyridaziniových solí při azokopulaci N-substituovaných 3-Amino-1-fenylbut-2-en-1-onů a diazoniových solí

Czech description

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.

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/GA203%2F03%2F0356" target="_blank" >GA203/03/0356: Tautomerism and hydrogen bonding in beta-eneminone derivatives. Multinuclear and X-ray study</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2004

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Volume of the periodical

Neuveden

Issue of the periodical within the volume

24

Country of publishing house

DE - GERMANY

Number of pages

9

Pages from-to

5055-5063

UT code for WoS article

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EID of the result in the Scopus database

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