Chain length dependent reactivity of 2-(ω-hydroxyalkyl)-4-(ω-hydroxyalkylamino)phthalazin-1(2h)-ones in azeotropic hydrobromic acid

A. Csámpai, K. Körmendy, F. Ruff

Research output: Article

30 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4457-4464
Number of pages8
JournalTetrahedron
Volume47
Issue number25
DOIs
Publication statusPublished - 1991

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Hydrobromic Acid
Alkalinity
Chain length
Boiling liquids
Molecules
Experiments
hydroxide ion

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Chain length dependent reactivity of 2-(ω-hydroxyalkyl)-4-(ω-hydroxyalkylamino)phthalazin-1(2h)-ones in azeotropic hydrobromic acid",
abstract = "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.",
author = "A. Cs{\'a}mpai and K. K{\"o}rmendy and F. Ruff",
year = "1991",
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language = "English",
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T1 - Chain length dependent reactivity of 2-(ω-hydroxyalkyl)-4-(ω-hydroxyalkylamino)phthalazin-1(2h)-ones in azeotropic hydrobromic acid

AU - Csámpai, A.

AU - Körmendy, K.

AU - Ruff, F.

PY - 1991

Y1 - 1991

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4020(01)87114-3

DO - 10.1016/S0040-4020(01)87114-3

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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