Nitrosylsulfuric acid in the synthesis of 5-chloroisoxazoles from 1,1-dichlorocyclopropanes

被引：5

作者：

Bondarenko, Oksana B. ^{[1
]}

Garaev, Zaur M. ^{[1
]}

Komarov, Arseniy I. ^{[1
]}

Kuznetsova, Lyubov I. ^{[1
]}

Gutorova, Svetlana V. ^{[1
]}

Skvortsov, Dmitry A. ^{[1
]}

Zyk, Nikolai V. ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

来源：

MENDELEEV COMMUNICATIONS | 2019年 / 29卷 / 04期

基金：

俄罗斯基础研究基金会;

关键词：

NITROSATION;

D O I：

10.1016/j.mencom.2019.07.021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nitrosylsulfuric acid is shown to be a usable reagent for the synthesis of 5-chioroisoxazoles from readily available 1,1-dichlorocyclopropanes via nitrosation-heterocyclization reaction. A cytotoxicity of some of the prepared 5-chloroisoxazoles towards MCF7, A549, HEK293T and VA13 cell lines was evaluated.

引用

页码：419 / 420

页数：2

共 17 条

[1] Synthesis of 5-aminoisoxazoles from 3-trimethylsilylprop-2-ynamides [J].

Andreev, Mikhail V. ;

Medvedeva, Alevtina S. ;

Larina, Lyudmila I. ;

Demina, Maria M. .

MENDELEEV COMMUNICATIONS, 2017, 27 (02) :175-177

[2] Nitrosylsulfuric acid as an oxidant in the synthesis of 3,5-diarylisoxazoles [J].

Bondarenko, O. B. ;

Komarov, A. I. ;

Kuznetsova, L. I. ;

Nikolaeva, S. N. ;

Gavrilova, A. Yu. ;

Zyk, N. V. .

RUSSIAN CHEMICAL BULLETIN, 2018, 67 (03) :517-520

[3] Nitrosation of adamantyl dichlorocyclopropanes as a new approach to adamantyl isoxazoles [J].

Bondarenko, O. B. ;

Baimuratov, M. R. ;

Klimochkin, Yu. N. ;

Zyk, N. V. .

RUSSIAN CHEMICAL BULLETIN, 2017, 66 (02) :376-378

[4] Transformations of gem-dichloroarylcyclopropanes in the reaction with NOCl•2SO3. Synthesis of 3-aryl-5-chloroisoxazoles [J].

Bondarenko, O. B. ;

Gavrilova, A. Yu. ;

Murodov, D. S. ;

Zefirov, N. S. ;

Zyk, N. V. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (02) :186-194

[5]

Bondarenko O. B., 2017, RF Patent, Patent No. 2637927

[6] Nitrosation of 2-aryl-1,1-dibromocyclopropanes: synthesis of 3-aryl-5-bromoisoxazoles [J].

Bondarenko, Oksana B. ;

Vinogradov, Aleksandr A. ;

Danilov, Pavel A. ;

Nikolaeva, Svetlana N. ;

Gavrilova, Anna Yu. ;

Zyk, Nikolai V. .

TETRAHEDRON LETTERS, 2015, 56 (47) :6577-6579

[7] New system for nitrosation of alkyl-substituted gem-dichlorocyclopropanes [J].

Bondarenko, Oksana B. ;

Gavrilova, Anna Yu ;

Murodov, Dilovar S. ;

Zyk, Nikolai V. ;

Zefirov, Nikolai S. .

MENDELEEV COMMUNICATIONS, 2011, 21 (04) :188-189

[8] Recent advances in isoxazole chemistry [J].

Galenko, A. V. ;

Khlebnikov, A. F. ;

Novikov, M. S. ;

Pakalnis, V. V. ;

Rostovskii, N. V. .

RUSSIAN CHEMICAL REVIEWS, 2015, 84 (04) :335-377

[9] Reaction of halogenated cyclopropanes and nitrosyl cation: Preparation of isoxazoles [J].

Lin, ST ;

Kuo, SH ;

Yang, FM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) :5229-5231

[10] RAPID COLORIMETRIC ASSAY FOR CELLULAR GROWTH AND SURVIVAL - APPLICATION TO PROLIFERATION AND CYTO-TOXICITY ASSAYS [J].

MOSMANN, T .

JOURNAL OF IMMUNOLOGICAL METHODS, 1983, 65 (1-2) :55-63

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