Rhodium-Catalyzed Cycloadditions between 3-Diazoindolin-2-imines and 1,3-Dienes

被引：59

作者：

Lang, Bo ^{[1
]}

Zhu, Huangtianzhi ^{[1
]}

Wang, Chen ^{[1
]}

Lu, Ping ^{[1
]}

Wang, Yanguang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 07期

基金：

中国国家自然科学基金;

关键词：

AZAVINYL CARBENES; TERMINAL ALKYNES; N-SULFONYL-1,2,3-TRIAZOLES; 1-SULFONYL-1,2,3-TRIAZOLES; TRANSANNULATION; REARRANGEMENT; ANNULATION; REACTIVITY; ALKALOIDS; SKELETONS;

D O I：

10.1021/acs.orglett.7b00438

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Azepino[2,3-b]indoles were regioselectively prepared through rhodium-catalyzed formal aza-[4 + 3] cycloaddition between 3-diazoindolin-2-imines and 1,3-dienes in moderate to good yields. Using 2-[(trimethylsilyl)oxy]-1,3-butadiene as the diene component, azepino[2,3-b]indol-4(1H)-ones were constructed. Furthermore, the reactions of cyclic dienes, such as 1,3-cyclohexadiene and 1,3-cyclopentadiene, furnished the corresponding [3 + 2] cycloaddition products.

引用

页码：1630 / 1633

页数：4

共 34 条

[1] Conversion of Cyclic Ketones to 2,3-Fused Pyrroles and Substituted Indoles [J].

Alford, Joshua S. ;

Spangler, Jillian E. ;

Davies, Huw M. L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11712-11715

[2] 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

[3] Stereoselective 1,3-Insertions of Rhodium(II) Azavinyl Carbenes [J].

Chuprakov, Stepan ;

Worrell, Brady T. ;

Selander, Nicklas ;

Sit, Rakesh K. ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (01) :195-202

[4] Transannulation of 1-Sulfonyl-1,2,3-triazoles with Heterocumulenes [J].

Chuprakov, Stepan ;

Kwok, Sen Wai ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) :4652-4655

[5] 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

[6] 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-+

[7] Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles [J].

Davies, Huw M. L. ;

Alford, Joshua S. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (15) :5151-5162

[8]

Gribble G.W., 2010, Heterocyclic Scaffolds II Topics in Heterocyclic Chemistry, Vol, V26

[9] Synthesis and Reactivity of Rhodium(II) N-Triflyl Azavinyl Carbenes [J].

Grimster, Neil ;

Zhang, Li ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) :2510-+

[10] Versatile Reactivity of Rhodium-Iminocarbenes Derived from N-Sulfonyl Triazoles [J].

Gulevich, Anton V. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1371-1373

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