Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole

被引：88

作者：

Wang, Ming ^{[1
]}

Fan, Qaoling ^{[1
]}

Jiang, Xuefeng ^{[1
,2
]}

机构：

[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 01期

关键词：

PALLADIUM-CATALYZED SYNTHESIS; C-H FUNCTIONALIZATION; UNSYMMETRICAL ACRIDINES; BOND AMINATION; ARYLATION; REAGENTS; STRATEGY; ANILINES;

D O I：

10.1021/acs.orglett.7b03564

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nitrogen iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a non steroidal anti-inflammatory drug) were efficiently established through this protocol.

引用

页码：216 / 219

页数：4

共 58 条

[21] CARAZOLOL, AN EXTREMELY POTENT BETA-ADRENERGIC BLOCKER - BINDING TO BETA-RECEPTORS IN BRAIN MEMBRANES [J].

INNIS, RB ;

CORREA, FMA ;

SNYDER, SH .

LIFE SCIENCES, 1979, 24 (24) :2255-2264

[22] Oxidative Pd(II)-Catalyzed C-H Bond Amination to Carbazole at Ambient Temperature [J].

Jordan-Hore, James A. ;

Johansson, Carin C. C. ;

Gulias, Moises ;

Beck, Elizabeth M. ;

Gaunt, Matthew J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (48) :16184-+

[23] Synthesis of Some Novel Pyrazole-Substituted 9-Anilinoacridine Derivatives and Evaluation for their Antioxidant and Cytotoxic Activities [J].

Kalirajan, R. ;

Muralidharan, V. ;

Jubie, S. ;

Gowramma, B. ;

Gomathy, S. ;

Sankar, S. ;

Elango, K. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (04) :748-754

[24] Pioneering Metal-Free Oxidative Coupling Strategy of Aromatic Compounds Using Hypervalent Iodine Reagents [J].

Kita, Yasuyuki ;

Dohi, Toshifumi .

CHEMICAL RECORD, 2015, 15 (05) :886-906

[25] Isolation and synthesis of biologically active carbazole alkaloids [J].

Knölker, HJ ;

Reddy, KR .

CHEMICAL REVIEWS, 2002, 102 (11) :4303-4427

[26] Facile Synthesis of Unsymmetrical Acridines and Phenazines by a Rh(III)-Catalyzed Amination/Cyclization/Aromatization Cascade [J].

Lian, Yajing ;

Hummel, Joshua R. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (34) :12548-12551

[27] Preparation of polyfunctional arylmagnesium reagents bearing a triazene moiety. A new carbazole synthesis [J].

Liu, CY ;

Knochel, P .

ORGANIC LETTERS, 2005, 7 (13) :2543-2546

[28] Mild Cu(I)-Catalyzed Cascade Reaction of Cyclic Diaryliodoniums, Sodium Azide, and Alkynes: Efficient Synthesis of Triazolophenanthridines [J].

Liu, Zhenquan ;

Zhu, Daqian ;

Luo, Bingling ;

Zhang, Naiyuan ;

Liu, Qi ;

Hu, Yumin ;

Pi, Rongbiao ;

Huang, Peng ;

Wen, Shijun .

ORGANIC LETTERS, 2014, 16 (21) :5600-5603

[29] Design, synthesis, and biological activity of a novel non-cisplatin-type platinum-acridine pharmacophore [J].

Martins, ET ;

Baruah, H ;

Kramarczyk, J ;

Saluta, G ;

Day, CS ;

Kucera, GL ;

Bierbach, U .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (25) :4492-4496

[30] Solvent-Free Heterocyclic Synthesis [J].

Martins, Marcos A. P. ;

Frizzo, Clarissa P. ;

Moreira, Dayse N. ;

Buriol, Lilian ;

Machado, Pablo .

CHEMICAL REVIEWS, 2009, 109 (09) :4140-4182

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