Direct Arylation of Sydnones with Aryl Chlorides toward Highly Substituted Pyrazoles

被引：22

作者：

Brown, Andrew W. ^{[1
]}

Harrity, Joseph P. A. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 04期

关键词：

REGIOSELECTIVE SYNTHESIS; CYCLOADDITION; ALKYNES; SCOPE;

D O I：

10.1021/acs.joc.5b00143

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct arylation of the C4 position of both N-alkyl- and N-arylsydnones with aryl/heteroaryl chlorides has been realized. The reaction is quite general and allows access to a wide range of 4-substituted sydnones. Yields of more challenging substrates can be improved through the use of aryl bromides.

引用

页码：2467 / 2472

页数：6

共 23 条

[1] A sydnone cycloaddition route to pyrazole boronic esters [J].

Browne, Duncan L. ;

Helm, Matthew D. ;

Plant, Andrew ;

Harrity, Joseph P. A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (45) :8656-8658

[2] Alkyne [3+2] Cycloadditions of Iodosydnones Toward Functionalized 1,3,5-Trisubstituted Pyrazoles [J].

Browne, Duncan L. ;

Taylor, John B. ;

Plant, Andrew ;

Harrity, Joseph P. A. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :984-987

[3] Investigation of the Scope and Regiochemistry of Alkynylboronate Cycloadditions with Sydnones [J].

Browne, Duncan L. ;

Vivat, Jerome F. ;

Plant, Andrew ;

Gomez-Bengoa, Enrique ;

Harrity, Joseph P. A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7762-7769

[4] Cross Coupling of Bromo Sydnones: Development of a Flexible Route toward Functionalized Pyrazoles [J].

Browne, Duncan L. ;

Taylor, John B. ;

Plant, Andrew ;

Harrity, Joseph P. A. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) :396-400

[5] Cu-Promoted Sydnone Cycloadditions of Alkynes: Scope and Mechanism Studies [J].

Comas-Barcelo, Julia ;

Foster, Robert S. ;

Fiser, Bela ;

Gomez-Bengoa, Enrique ;

Harrity, Joseph P. A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (08) :3257-3263

[6] Copper(I)-Catalyzed Cycloaddition of 4-Bromosydnones and Alkynes for the Regioselective Synthesis of 1,4,5-Trisubstituted Pyrazoles [J].

Decuypere, Elodie ;

Specklin, Simon ;

Gabillet, Sandra ;

Audisio, Davide ;

Liu, Hui ;

Plougastel, Lucie ;

Kolodych, Sergii ;

Taran, Frederic .

ORGANIC LETTERS, 2015, 17 (02) :362-365

[7] Synthesis of 4-Fluoromethylsydnones and their Participation in Alkyne Cycloaddition Reactions [J].

Foster, Robert S. ;

Adams, Harry ;

Jakobi, Harald ;

Harrity, Joseph P. A. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08) :4049-4064

[8] A General and Regioselective Synthesis of 5-Trifluoromethyl-pyrazoles [J].

Foster, Robert S. ;

Jakobi, Harald ;

Harrity, Joseph P. A. .

ORGANIC LETTERS, 2012, 14 (18) :4858-4861

[9] Mechanistic studies on the aryl-aryl interchange reaction of ArPdL2I (L = triarylphosphine) complexes [J].

Goodson, FE ;

Wallow, TI ;

Novak, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (51) :12441-12453

[10] SYNTHESIS OF ARYL-SYDNONE AND VINYL-SYDNONE - CROSS-COUPLING OF 4-COPPER-3-PHENYLSYDNONE WITH ARYL AND VINYL HALIDES CATALYZED BY PALLADIUM(0) COMPLEXES [J].

KALININ, VN ;

MIN, SF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 352 (1-2) :C34-C36

← 1 2 3 →