135486-45-2Relevant academic research and scientific papers
Chain length dependent reactivity of 2-(ω-hydroxyalkyl)-4-(ω'-hydroxyalkylamino)phthalazin-1(2H)-ones in azeotropic hydrobromic acid
Csampai,Kormendy,Ruff
, p. 4457 - 4464 (2007/10/02)
In boiling 48% HBr conversions of title compounds (5a-f) resulted in 2-(ω-bromoalkyl)-4-(2-hydroxyethylamino)-phthalazinones 8a,c, angular tricycles 7a,c-f and the 14a tricyclic dione, respectively, depending on the lengths of the side chains and the reaction time applied. The large difference between the reactivities of 4-(2-hydroxyethylamino)- and 4-(3-hydroxypropylamino) homologues in the exchange OH → Br was interpreted on the basis of the relative OH-basicities in the N3-protonated molecules. The proposed mechanism for the conversion to 14a involving a Smiles-type rearrangement was supported by additional experiments with 4-amino-2-(ω-hydroxyalkyl)-phthalazinones 15a,b.
