Investigation of Chemoselective Reaction of 2-Amino-8-hydroxyquinoline with Arylsulfonylchloride Derivatives

doi:10.1080/00397910802527730

Paper

Investigation of Chemoselective Reaction of 2-Amino-8-hydroxyquinoline with Arylsulfonylchloride Derivatives

Published Mar 19, 2009 · Luiz Everson Da Silva, Paulo Teixieira De Sousa, Antonio Carlos Joussef

Synthetic Communications

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Abstract

Abstract The reactions of 2-amino-8-hydroxyquinoline and 2-amino-4(1H)quinolone with different sulfonyl chlorides have been investigated. The chemoselectivity was observed to afford exclusively the arylsulfonate ester derivatives. The mechanism of the reaction is also discussed.

Study Snapshot

The chemoelective reaction of 2-amino-8-hydroxyquinoline and 2-amino-4(1H)quinolone with sulfonyl chlorides exclusively affords arylsulfonate ester derivatives, with a mechanism discussed.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Investigation of Chemoselective Reaction of 2-Amino-8-hydroxyquinoline with Arylsulfonylchloride Derivatives

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References

Synthesis and in vitro evaluation of leishmanicidal and trypanocidal activities of N-quinolin-8-yl-arylsulfonamides.

N-quinolin-8-yl-arylsulfonamides show high leishmanicidal and trypanocidal activities against Leishmania amazonensis, Leishmania chagasi, and Trypanosoma cruzi strains, with the most active compound being N-(

2-Aminoquinolin-4-yl 2,4,6-triisopropylbenzenesulfonate

The molecular packing of 2-aminoquinolin-4-yl 2,4,6-triisopropylbenzenesulfonate is stabilized by a hydrogen-bonded network, with both sulfonyl O atoms involved in intermolecular hydrogen bonds.

Fluorogenic Hg2+-selective chemodosimeter derived from 8-hydroxyquinoline.

The new thioamide derivative of 8-hydroxyquinoline-benzothiazole shows highly Hg2+-selective fluorescence enhancing properties, with sensitive signaling behaviors originating from the transformation of the weak fluorescent thioamide derivative into a highly fluorescent amide analogue.

Comparison of protective effects against reactive oxygen species of mononuclear and dinuclear Cu(II) complexes with N-substituted benzothiazolesulfonamides.

Mononuclear copper(II) complexes with N-substituted benzothiazolesulfonamides show better protective effects against reactive oxygen species than dinuclear complexes, but dimeric complexes are better SOD mimics in vitro.

Synthesis and characterisation of soluble aluminium complex dyes based on 5-substituted-8-hydroxyquinoline derivatives for OLED applications

New 5-substituted-8-hydroxyquinoline derivatives show high fluorescence quantum yield and potential for OLED applications, with a turn-on voltage of about 11 V.

Citations

Chemoselective synthesis of 5-amino-7-bromoquinolin-8-yl sulfonate derivatives and their antimicrobial evaluation

The synthesized compounds show potent antibacterial and antifungal activities, with 5-amino-7-bromoquinolin-8-yl biphenyl-4-sulfonate showing the highest antifungal activity.

Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters

Chemoselective acylation of 2-amino-8-quinolinol can generate C2-amides and C8-esters, with unique features like coupling reactions with various carboxylic acids and selective treatment of anionic nucleophiles.

Synthesis, structural characterization and leishmanicidal activity evaluation of ferrocenyl N-heterocyclic compounds

New ferrocenyl N-heterocyclic compounds show promising leishmanicidal activity against Leishmania infantum parasites, with compounds 3 and 9 showing significantly better therapeutic indexes than control miltefosine.

Investigation of Chemoselective Reaction of 2-Amino-8-hydroxyquinoline with Arylsulfonylchloride Derivatives

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References

Synthesis and in vitro evaluation of leishmanicidal and trypanocidal activities of N-quinolin-8-yl-arylsulfonamides.

N-quinolin-8-yl-arylsulfonamides show high leishmanicidal and trypanocidal activities against Leishmania amazonensis, Leishmania chagasi, and Trypanosoma cruzi strains, with the most active compound being N-(

2-Amino­quinolin-4-yl 2,4,6-triisopropyl­benzene­sulfonate

The molecular packing of 2-aminoquinolin-4-yl 2,4,6-triisopropylbenzenesulfonate is stabilized by a hydrogen-bonded network, with both sulfonyl O atoms involved in intermolecular hydrogen bonds.

Fluorogenic Hg2+-selective chemodosimeter derived from 8-hydroxyquinoline.

The new thioamide derivative of 8-hydroxyquinoline-benzothiazole shows highly Hg2+-selective fluorescence enhancing properties, with sensitive signaling behaviors originating from the transformation of the weak fluorescent thioamide derivative into a highly fluorescent amide analogue.

Comparison of protective effects against reactive oxygen species of mononuclear and dinuclear Cu(II) complexes with N-substituted benzothiazolesulfonamides.

Mononuclear copper(II) complexes with N-substituted benzothiazolesulfonamides show better protective effects against reactive oxygen species than dinuclear complexes, but dimeric complexes are better SOD mimics in vitro.

Synthesis and characterisation of soluble aluminium complex dyes based on 5-substituted-8-hydroxyquinoline derivatives for OLED applications

New 5-substituted-8-hydroxyquinoline derivatives show high fluorescence quantum yield and potential for OLED applications, with a turn-on voltage of about 11 V.

Citations

Chemoselective synthesis of 5-amino-7-bromoquinolin-8-yl sulfonate derivatives and their antimicrobial evaluation

The synthesized compounds show potent antibacterial and antifungal activities, with 5-amino-7-bromoquinolin-8-yl biphenyl-4-sulfonate showing the highest antifungal activity.

Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters

Chemoselective acylation of 2-amino-8-quinolinol can generate C2-amides and C8-esters, with unique features like coupling reactions with various carboxylic acids and selective treatment of anionic nucleophiles.

Synthesis, structural characterization and leishmanicidal activity evaluation of ferrocenyl N-heterocyclic compounds

New ferrocenyl N-heterocyclic compounds show promising leishmanicidal activity against Leishmania infantum parasites, with compounds 3 and 9 showing significantly better therapeutic indexes than control miltefosine.

2-Aminoquinolin-4-yl 2,4,6-triisopropylbenzenesulfonate