A Mild and Regiospecific Synthesis of Pyrazoleboranes

被引：23

作者：

Brown, Andrew W. ^{[1
]}

Comas-Barcelo, Julia ^{[1
]}

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

机构：

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 22期

关键词：

alkynylborane; cycloaddition; pyrazole; regioselective; sydnone; DIRECTED CYCLOADDITION; CHEMISTRY; SYDNONES; ALKYNES; SCOPE;

D O I：

10.1002/chem.201701019

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkynylboranes show unprecedented reactivity in their [4+2] cycloaddition of sydnones offering access to fully substituted pyrazoles within a few hours at room temperature. This method delivers synthetically valuable pyrazoleboranes with complete control of regioselectivity, and these intermediates can be further elaborated through functionalization of the C-B bond.

引用

页码：5228 / 5231

页数：4

共 20 条

[1] Development of a Mild and Versatile Directed Cycloaddition Approach to Pyridines [J].

Bachollet, Sylvestre P. J. T. ;

Vivat, Jerome F. ;

Cocker, Dean C. ;

Adams, Harry ;

Harrity, Joseph P. A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (40) :12889-12893

[2] Sydnone Cycloaddition Route to Pyrazole-Based Analogs of Combretastatin A4 [J].

Brown, Andrew W. ;

Fisher, Matthew ;

Tozer, Gillian M. ;

Kanthou, Chryso ;

Harrity, Joseph P. A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (20) :9473-9488

[3] Recent developments in the chemistry of sydnones [J].

Browne, Duncan L. ;

Harrity, Joseph P. A. .

TETRAHEDRON, 2010, 66 (03) :553-568

[4] 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

[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] A Mechanistic Study of the Lewis Base-Directed Cycloaddition of 2-Pyrones and Alkynylboranes [J].

Crepin, Damien F. P. ;

Harrity, Joseph P. A. ;

Jiang, Julong ;

Meijer, Anthony J. H. M. ;

Nassoy, Anne-Chloe M. A. ;

Raubo, Piotr .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) :8642-8653

[7] 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

[8] [1,3]-Dipolar cycloaddition of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)-1H-indole [J].

Durust, Yasar ;

Sagirli, Akin ;

Kariuki, Benson M. ;

Knight, David W. .

TETRAHEDRON, 2014, 70 (35) :6012-6019

[9] 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

[10] From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles [J].

Fustero, Santos ;

Sanchez-Rosello, Maria ;

Barrio, Pablo ;

Simon-Fuentes, Antonio .

CHEMICAL REVIEWS, 2011, 111 (11) :6984-7034

← 1 2 →