R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and Beyond

被引：10

作者：

Bondarenko, Oksana B. ^{[1
]}

Karetnikov, Georgy L. ^{[1
]}

Komarov, Arseniy, I ^{[1
]}

Pavlov, Aleksandr, I ^{[1
]}

Nikolaeva, Svetlana N. ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期

基金：

俄罗斯基础研究基金会;

关键词：

REGIOSELECTIVE IODINATION; NITROSYLSULFURIC ACID; AROMATIC-COMPOUNDS; EFFICIENT METHOD; NITROGEN-OXIDE; C-13; NMR; MILD; CONVENIENT; BROMINATION; 3,5-DIARYLISOXAZOLES;

D O I：

10.1021/acs.joc.0c02106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new convenient and versatile halogenating system (R(4)NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.

引用

页码：322 / 332

页数：11

共 58 条

[1]

Barluenga J., 1987, J CHEM RES, V7, P1763

[2] Iodine(I) Reagents in Hydrochloric Acid-Catalyzed Oxidative Iodination of Aromatic Compounds by Hydrogen Peroxide and Iodine [J].

Bedrac, Leon ;

Iskra, Jernej .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) :1243-1248

[3]

Belenkii L. I., 1997, CHEM HET COMPUT, V32, P1319

[4] Nitrosylsulfuric acid as a tandem reagent in the synthesis of 3,5-diarylisoxazoles from 1,2-diarylcyclopropanes [J].

Bondarenko, O. B. ;

Komarov, A., I ;

Karetnikov, G. L. ;

Nikolaeva, S. N. ;

Zyk, N., V .

RUSSIAN CHEMICAL BULLETIN, 2019, 68 (06) :1200-1203

[5] 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

[6] Transformations of gem-dibromoarylcyclopropanes under nitrosation conditions on treatment with NOCl•(SO3)n [J].

Bondarenko, O. B. ;

Gavrilova, A. Yu. ;

Nikolaeva, S. N. ;

Zyk, N. V. .

RUSSIAN CHEMICAL BULLETIN, 2016, 65 (05) :1225-1231

[7]

Bondarenko O. B., 2020, OFFICIAL B FEDERAL S, Patent No. 2711558

[8] Nitrosylsulfuric acid in the synthesis of 5-chloroisoxazoles from 1,1-dichlorocyclopropanes [J].

Bondarenko, Oksana B. ;

Garaev, Zaur M. ;

Komarov, Arseniy I. ;

Kuznetsova, Lyubov I. ;

Gutorova, Svetlana V. ;

Skvortsov, Dmitry A. ;

Zyk, Nikolai V. .

MENDELEEV COMMUNICATIONS, 2019, 29 (04) :419-420

[9] 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

[10] Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid [J].

Castanet, AS ;

Colobert, F ;

Broutin, PE .

TETRAHEDRON LETTERS, 2002, 43 (29) :5047-5048

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