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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

✍ Scribed by Petr Šimůnek; Markéta Pešková; Valerio Bertolasi; Antonín Lyčka; Vladimír Macháček

Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 167 KB
Volume: 2004
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200400287

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✦ Synopsis

Abstract

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 ^1^H, ^13^C, ^15^N, ^11^B and ^19^F 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)

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