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DOI: 10.1055/s-2008-1067269
A New Synthesis of Bis-Enaminones via Acylation of Ketones
Publikationsverlauf
Publikationsdatum:
05. September 2008 (online)
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Abstract
A short and efficient synthesis for a series of 1,6-diaryl-3,4-diarylaminohexa-2,4-diene-1,6-diones was developed. Based on the acylation-prototropism sequence during the reaction of various aryl methyl ketones with bis-imidoyl chlorides, the products were isolated in good yields. Substituted acetophenones, acetylthiophene, 3-acetylpyridine, and acetylferrocene can be integrated into this reaction as ketone component. Similarly, α-tetralone can be transformed with bis-electrophiles into the corresponding bis-enaminones. Treatment of 2-acetylpyridine with N,N′-bis(4-tolyl)ethanebis(imidoyl) dichloride yielded not only the expected bis-enaminone, but also a new quinolizine derivative which was structurally characterized by single crystal X-ray analysis. Analogously, pinacolone and cyclopropyl methyl ketone can readily be converted into bis-enaminones. Monoimidoyl chlorides showed the same reactivity, providing derivatives in high yields.
Key words
acylations - ketones - tautomerism - enaminones - bis-imidoyl chlorides
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References
Derivatives 2 melt under the formation of dark green liquids; at about 260 ˚C formation of a colorless liquid takes place.
12CCDC-688639 (2e) and CCDC-688640 (7) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; or deposit@ccdc.cam.ac.uk).