Visible light amination/Smiles cascade: access to phthalazine derivatives

被引：99

作者：

Brachet, Etienne ^{[1
]}

Marzo, Leyre ^{[2
]}

Selkti, Mohamed ^{[3
]}

Koenig, Burkhard ^{[2
]}

Belmont, Philippe ^{[1
]}

机构：

[1] Univ Paris 05, USPC, Fac Pharm Paris, UMR CNRS COMETE 8638, 4 Ave Observ, F-75006 Paris, France

[2] Univ Regensburg, Fac Chem & Pharm, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany

[3] Univ Paris 05, USPC, Fac Pharm Paris, UMR CNRS LCRB 8015, 4 Ave Observ, F-75006 Paris, France

来源：

CHEMICAL SCIENCE | 2016年 / 7卷 / 08期

关键词：

C-H AMINATION; PHOTOREDOX; RADICALS; ALKENES; TRANSITION; HYDROAMINATION; REARRANGEMENT; HETEROCYCLES; CYCLIZATION; AMIDATION;

D O I：

10.1039/c6sc01095d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the synthesis of various phthalazines via a new cascade reaction, initiated by visible light photocatalysis, involving a radical hydroamination reaction followed by a radical Smiles rearrangement. Phthalazine derivatives are obtained in high yields and from a broad scope readily accessible orthoalkynylsulfonohydrazone precursors. The mild photoredox conditions ensure an excellent functional group tolerance. Application of this strategy to a one-pot protocol starting from the corresponding carbonyl compounds, and subsequent functionalization allow the rapid synthesis of structurally diverse structures.

引用

页码：5002 / 5006

页数：5

共 57 条

[1] N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes [J].

Allen, Laura J. ;

Cabrera, Pablo J. ;

Lee, Melissa ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) :5607-5610

[2]

Asif M, 2012, CURR MED CHEM, V19, P2984

[3] Visible light C-H amidation of heteroarenes with benzoyl azides [J].

Brachet, E. ;

Ghosh, T. ;

Ghosh, I. ;

Koenig, B. .

CHEMICAL SCIENCE, 2015, 6 (02) :987-992

[4] A palladium-catalyzed coupling of 3-chloroquinoxalinones with various nitrogen-containing nucleophiles [J].

Brachet, Etienne ;

Peyrat, Jean-Francois ;

Brion, Jean-Daniel ;

Messaoudi, Samir ;

Alami, Mouad .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (23) :3808-3816

[5] Indole, a core nucleus for potent inhibitors of tubulin polymerization [J].

Brancale, Andrea ;

Silvestri, Romano .

MEDICINAL RESEARCH REVIEWS, 2007, 27 (02) :209-238

[6] Synthesis and Application of Palladium Precatalysts that Accommodate Extremely Bulky Di-tert-butylphosphino Biaryl Ligands [J].

Bruno, Nicholas C. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2013, 15 (11) :2876-2879

[7] Enantioselective Direct α-Annination of Aldehydes via a Photoredox Mechanism: A Strategy for Asymmetric Amine Fragment Coupling [J].

Cecere, Giuseppe ;

Koenig, Christian M. ;

Alleva, Jennifer L. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (31) :11521-11524

[8] Visible light photoredox-controlled reactions of N-radicals and radical ions [J].

Chen, Jia-Rong ;

Hu, Xiao-Qiang ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056

[9] Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles [J].

Chen, Jia-Rong ;

Yu, Xiao-Ye ;

Xiao, Wen-Jing .

SYNTHESIS-STUTTGART, 2015, 47 (05) :604-629

[10] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

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