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Synthsis and properties of azulene-containing dioxane

Domenii publicaţii > Chimie + Tipuri publicaţii > Articol în revistã ştiinţificã

Autori: Alexandru C. Razus, Liviu Birzan, Liliana Cristian, Victorita Tecuceanu

Editorial: Arkivoc, xi, p.31-44, 2009.


[1,3]Dioxane-4,6-diones with (azulen-1-yl)methylene attached to position 5 were obtained by condensation of azulene-1-carbaldehydes with Meldrum’s acid. The reaction was performed either neat or in absolute ethanol using a base as a catalyst. The involvement of the generated C=C bond either in electrophilic or radical reactions appears to be restricted. The advanced molecular polarization of the obtained products can account for the low reactivity of this bond. With the electrophilic reagents only the 3-position of azulenyl moiety was substituted. The azulene acylation with acetylsalicyloyl chloride occurred with rearrangement of the acyl chloride and, the formed products are 4H-1,3-benzodioxin-4-ones where azulen-1-yl moiety occupies the position 2 of the heterocyclic system.

Cuvinte cheie: Azulene, [1,3]dioxane-4,6-dione, 4H-1,3-benzodioxin-4-ones, Meldrum’s acid