Transannulation of 1-Sulfonyl-1,2,3-triazoles with Heterocumulenes

被引：207

作者：

Chuprakov, Stepan ^{[1
]}

Kwok, Sen Wai ^{[1
]}

Fokin, Valery V. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 12期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

RHODIUM(II) AZAVINYL CARBENES; RH-CATALYZED TRANSANNULATION; H INSERTION REACTIONS; TERMINAL ALKYNES; REACTIVITY; N-SULFONYL-1,2,3-TRIAZOLES; CYCLOPROPANATION; 1,2,3-TRIAZOLES; REARRANGEMENTS; DIRHODIUM(II);

D O I：

10.1021/ja400350c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.

引用

页码：4652 / 4655

页数：4

共 31 条

[1] Expanding the Scope of Donor/Acceptor Carbenes to N-Phthalimido Donor Groups: Diastereoselective Synthesis of 1-Cyclopropane α-Amino Acids [J].

Alford, Joshua S. ;

Davies, Huw M. L. .

ORGANIC LETTERS, 2012, 14 (23) :6020-6023

[2] SYNTHESIS OF 1,3-OXATHIOLE AND 2(3H)-OXAZOLONE DERIVATIVES BY CYCLOADDITION OF ALPHA-KETO CARBENOIDS TO HETEROCUMULENES [J].

BIEN, S ;

KIMMEL, T ;

TIROSH, N .

ACTA CHEMICA SCANDINAVICA, 1993, 47 (02) :218-220

[3] Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems [J].

Chattopadhyay, Buddhadeb ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :862-872

[4] Rh-Catalyzed Transannulation of N-Tosyl-1,2,3-Triazoles with Terminal Alkynes [J].

Chattopadhyay, Buddhadeb ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2011, 13 (14) :3746-3749

[5] Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles [J].

Chuprakov, Stepan ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2007, 9 (22) :4463-4466

[6] Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles [J].

Chuprakov, Stepan ;

Hwang, Frank W. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4757-4759

[7] Catalytic Asymmetric C-H Insertions of Rhodium(II) Azavinyl Carbenes [J].

Chuprakov, Stepan ;

Malik, Jamal A. ;

Zibinsky, Mikhail ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10352-10355

[8] Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with N-Sulfonyl 1,2,3-Triazoles [J].

Chuprakov, Stepan ;

Kwok, Sen Wai ;

Zhang, Li ;

Lercher, Lukas ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (50) :18034-+

[9]

DIMROTH O, 1909, LIEBIGS ANN CHEM, V364, P183

[10]

DRAPIER J, 1979, TETRAHEDRON LETT, P559

← 1 2 3 4 →