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Synthesis 2003(10): 1620-1625
DOI: 10.1055/s-2003-40528
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Reactions of (1E,2Z)-2-N,N-Dialkylhydrazono-2-phenylethanal N,N-Dimethylhydrazones

Rainer Brehme*a, Günter Reckb, Burkhard Schulzb, Reiner Radegliab
a Max-Planck-Institut für Kolloid- und Grenzflächenforschung, Abt. Grenzflächen, 14424 Potsdam, Germany
b Bundesanstalt für Materialforschung und -prüfung, Richard-Willstätter-Straße 11, 12489 Berlin, Germany
Fax: +49(30)81045927; e-Mail: guenter.reck@bam.de;
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Publication History

Received 19 December 2002
Publication Date:
08 July 2003 (online)

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Abstract

(1E,2Z)-2-N,N-Dialkylhydrazono-2-phenylethanal N,N-dimethylhydrazones 3a-e were synthesised by the reaction of 1,4,5-triazapentadienium salts 2 with N,N-dimethylhydrazine. The compounds 3a and 3d did not react with tosyl isocyanate in an electrophilic substitution reaction at the azomethine C-1 as aza-enamines, but they reacted at room temperature in benzene in a 1,4-dipolar cycloaddition to yield 1,3,5-triazinan-2,4-diones 5a and 5d, whereas at 70 °C octahydroimidazoimidazol-2,5-dione 6a was formed via criss-cross addition reaction. With dimethyl sulfate in DMF, 3a was transformed into the trimethylhydrazonium salts 7a and 8a, isolated as co-crystallised perchlorates (molar ratio 1:1).

Key words

aza-enamines - heterocycles - hydrazonium salts - 1,4-dipolar cycloaddition - criss-cross addition reaction