Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide

Vasilii E. Evtushok; Aleksey Yu Vorob’ev

doi:10.1007/s10593-019-02446-0

Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide

Vasilii E. Evtushok, Aleksey Yu Vorob’ev

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The reaction of 1-amino-8-hydroxyquinolinium mesitylenesulfonate with alkenes and alkynes containing electron-withdrawing substituents was performed in MeCN–K ₂ СО ₃ system and gave the respective 9-hydroxypyrazolo[1,5-a]quinolines. The reaction with acetonitrile\ and aromatic nitriles in aqueous 2 N KОН solution gave the respective 2-substituted 9-hydroxy[1,2,4]triazolo[1,5-a]quinolines.

Original language	English
Pages (from-to)	229-234
Number of pages	6
Journal	Chemistry of Heterocyclic Compounds
Volume	55
Issue number	3
DOIs	https://doi.org/10.1007/s10593-019-02446-0
Publication status	Published - 15 Mar 2019

Keywords

1,3-dipolar cycloaddition
8-hydroxyquinoline
N-imines
pyrazolo[1,5-а]quinoline
[1,2,4]triazolo[1,5-а]quinoline
IMINES
5-a]quinoline
COMPLEXES
4]triazolo[1
2
CHEMOSENSOR
[1
1,3-DIPOLAR CYCLOADDITION
CHEMISTRY
pyrazolo[1
DERIVATIVES
SCAFFOLD

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10.1007/s10593-019-02446-0

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title = "Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide",

abstract = "The reaction of 1-amino-8-hydroxyquinolinium mesitylenesulfonate with alkenes and alkynes containing electron-withdrawing substituents was performed in MeCN–K 2 СО 3 system and gave the respective 9-hydroxypyrazolo[1,5-a]quinolines. The reaction with acetonitrile\ and aromatic nitriles in aqueous 2 N KОН solution gave the respective 2-substituted 9-hydroxy[1,2,4]triazolo[1,5-a]quinolines. ",

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author = "Evtushok, {Vasilii E.} and Vorob{\textquoteright}ev, {Aleksey Yu}",

year = "2019",

month = mar,

day = "15",

doi = "10.1007/s10593-019-02446-0",

language = "English",

volume = "55",

pages = "229--234",

journal = "Chemistry of Heterocyclic Compounds",

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publisher = "Springer New York",

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TY - JOUR

T1 - Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide

AU - Evtushok, Vasilii E.

AU - Vorob’ev, Aleksey Yu

PY - 2019/3/15

Y1 - 2019/3/15

N2 - The reaction of 1-amino-8-hydroxyquinolinium mesitylenesulfonate with alkenes and alkynes containing electron-withdrawing substituents was performed in MeCN–K 2 СО 3 system and gave the respective 9-hydroxypyrazolo[1,5-a]quinolines. The reaction with acetonitrile\ and aromatic nitriles in aqueous 2 N KОН solution gave the respective 2-substituted 9-hydroxy[1,2,4]triazolo[1,5-a]quinolines.

AB - The reaction of 1-amino-8-hydroxyquinolinium mesitylenesulfonate with alkenes and alkynes containing electron-withdrawing substituents was performed in MeCN–K 2 СО 3 system and gave the respective 9-hydroxypyrazolo[1,5-a]quinolines. The reaction with acetonitrile\ and aromatic nitriles in aqueous 2 N KОН solution gave the respective 2-substituted 9-hydroxy[1,2,4]triazolo[1,5-a]quinolines.

KW - 1,3-dipolar cycloaddition

KW - 8-hydroxyquinoline

KW - N-imines

KW - pyrazolo[1,5-а]quinoline

KW - [1,2,4]triazolo[1,5-а]quinoline

KW - IMINES

KW - 5-a]quinoline

KW - COMPLEXES

KW - 4]triazolo[1

KW - 2

KW - CHEMOSENSOR

KW - [1

KW - 1,3-DIPOLAR CYCLOADDITION

KW - CHEMISTRY

KW - pyrazolo[1

KW - DERIVATIVES

KW - SCAFFOLD

UR - http://www.scopus.com/inward/record.url?scp=85065392502&partnerID=8YFLogxK

U2 - 10.1007/s10593-019-02446-0

DO - 10.1007/s10593-019-02446-0

M3 - Article

AN - SCOPUS:85065392502

VL - 55

SP - 229

EP - 234

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 3

ER -

Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide

Abstract

Keywords

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