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

被引：8

作者：

Evtushok, Vasilii E. ^{[1
]}

Vorob'ev, Aleksey Yu. ^{[2
,3
]}

机构：

[1] Russian Acad Sci, Siberian Branch, Boreskov Inst Catalysis, 5 Akad Lavrentieva Ave, Novosibirsk 630090, Russia

[2] Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia

[3] Novosibirsk State Univ, 1 Pirogova St, Novosibirsk 630090, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2019年 / 55卷 / 03期

基金：

俄罗斯科学基金会;

关键词：

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

D O I：

10.1007/s10593-019-02446-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1-amino-8-hydroxyquinolinium mesitylenesulfonate with alkenes and alkynes containing electron-withdrawing substituents was performed in MeCN-K2C?(3) system and gave the respective 9-hydroxypyrazolo[1,5-a]quinolines. The reaction with acetonitrile\ and aromatic nitriles in aqueous 2 N K?H solution gave the respective 2-substituted 9-hydroxy[1,2,4]triazolo[1,5-a]quinolines.

引用

页码：229 / 234

页数：6

共 41 条

[31] 8-Hydroxyquinoline: a privileged structure with a broad-ranging pharmacological potential [J].

Song, Yu'ning ;

Xu, Hao ;

Chen, Wenmin ;

Zhan, Peng ;

Liu, Xinyong .

MEDCHEMCOMM, 2015, 6 (01) :61-74

[32] Study on selectivity in the reaction of 2-substituted pyridinium-N-imines with dimethyl acetylenedicarboxylate [J].

Supranovich, Vyacheslav I. ;

Vorob'ev, Aleksey Yu. ;

Borodkin, Gennady I. ;

Gatilov, Yury V. ;

Shubin, Vyacheslav G. .

TETRAHEDRON LETTERS, 2016, 57 (10) :1093-1096

[33] 1,3-DIPOLAR CYCLOADDITION REACTION OF BENZODIAZINIUM AND NAPHTHYRIDINIUM N-IMINES WITH ACETYLENIC ESTERS [J].

TAMURA, Y ;

MIKI, Y ;

IKEDA, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (01) :119-122

[34]

TAMURA Y, 1977, SYNTHESIS STUTTGART, V1

[35] Synthesis and Antitumor Activity of 2-Aryl-1, 2, 4-Triazolo[1, 5-a] Pyridine Derivatives [J].

Tao, Xuefen ;

Hu, Yongzhou .

MEDICINAL CHEMISTRY, 2010, 6 (02) :65-69

[36] The design of 8-hydroxyquinoline tetracyclic lactams as HIV-1 integrase strand transfer inhibitors [J].

Velthuisen, Emile J. ;

Johns, Brian A. ;

Temelkoff, David P. ;

Brown, Kevin W. ;

Danehower, Susan C. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 117 :99-112

[37]

Villemagne Victor L, 2017, Alzheimers Dement (N Y), V3, P622, DOI 10.1016/j.trci.2017.10.001

[38]

Vinogradov A. V., 1979, HYDROXYQUINOLINE

[39] Novel 8-hydroxyquinoline derivatives targeting β-amyloid aggregation, metal chelation and oxidative stress against Alzheimer's disease [J].

Yang, Xuelian ;

Cai, Pei ;

Liu, Qiaohong ;

Wu, Jiajia ;

Yin, Yong ;

Wang, Xiaobing ;

Kong, Lingyi .

BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (12) :3191-3201

[40] Clioquinol, an alternative antimicrobial agent against common pathogenic microbe [J].

You, Z. ;

Ran, X. ;

Dai, Y. ;

Ran, Y. .

JOURNAL DE MYCOLOGIE MEDICALE, 2018, 28 (03) :492-501

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