Chain length dependent reactivity of 2-(ω-hydroxyalkyl)-4-(ω-hydroxyalkylamino)phthalazin-1(2h)-ones in azeotropic hydrobromic acid
✍ Scribed by A. CsXmpai; K. Körmendy; F. Ruff
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 545 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
In boiling 48% HBr conversions of title compounds (&+-f) resulted in 2-(w-bromoalkyl)-4-(2-hydroxyethylamino)-phthalazrnones 8a,c, angular tricycles &s-C and the 14a &cyclic &one, respecirv:ly, depending on the lengths of the'fyde chains and the reaction time applred. The large diff;rence between the reactivrtres of 4-(2hydroxyethylamino)-and 4-(3-hydroxypropylamino) homologues in the exchange OH -c Br was interpreted on the basis of the relative OH-basrcitres rn the N3-protonated molecules. The proposed mechanism for the conversion to 142 involving a Smiles-type rearrangement was supported by additional experiments with 4-amino-2-(w-hydroxyalkyl)phthalasinones AZ&b.