Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-H-Phenanthridines via a Transition-Metal-Free Process

被引：57

作者：

Chen, Wei-Lin ^{[1
]}

Chen, Chun-Yuan ^{[1
]}

Chen, Yan-Fu ^{[1
]}

Hsieh, Jen-Chieh ^{[1
]}

机构：

[1] Tamkang Univ, Dept Chem, Taipei 25137, Taiwan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 06期

关键词：

NUCLEOPHILIC AROMATIC-SUBSTITUTION; COPPER-MEDIATED FLUORINATION; CASCADE RING-CLOSURE; C BOND FORMATION; O-PHENYL OXIMES; BENZOPHENANTHRIDINE ALKALOIDS; SCELETIUM ALKALOIDS; PALLADIUM CATALYSIS; IMINYL RADICALS; SNAR REACTIONS;

D O I：

10.1021/acs.orglett.5b00544

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (SNAr). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.

引用

收藏

页码：1613 / 1616

页数：4

相关论文

共 79 条

[1] New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines [J].

Alonso, Rafael ;

Campos, Pedro J. ;

Garcia, Barbara ;

Rodriguez, Miguel A. .

ORGANIC LETTERS, 2006, 8 (16) :3521-3523

[2] Photochemical study of tris(benzotriazol-1-yl)methane [J].

Androsov, Dmitry A. ;

Neckers, Douglas C. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1148-1152

[3] Catalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation-Directed Nucleophilic Aromatic Substitution Reaction [J].

Armstrong, Roly J. ;

Smith, Martin D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (47) :12822-12826

[4] NUCLEOPHILIC DISPLACEMENTS OF ACTIVATED FLUORINE IN AROMATIC COMPOUNDS [J].

BADER, H ;

HANSEN, AR ;

MCCARTY, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2319-&

[5] Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs [J].

Baechler, Simone A. ;

Fehr, Markus ;

Habermeyer, Michael ;

Hofmann, Andreas ;

Merz, Karl-Heinz ;

Fiebig, Heinz-Herbert ;

Marko, Doris ;

Eisenbrand, Gerhard .

BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (03) :814-823

[6] DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine [J].

Bai, Li-Ping ;

Zhao, Zhong-Zhen ;

Cai, Zongwei ;

Jiang, Zhi-Hong .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (16) :5439-5445

[7] Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters [J].

Banwell, MG ;

Lupton, DW ;

Ma, XH ;

Renner, J ;

Sydnes, MO .

ORGANIC LETTERS, 2004, 6 (16) :2741-2744

[8] NUCLEOPHILIC-SUBSTITUTION - LINEAR FREE-ENERGY RELATIONSHIPS BETWEEN REACTIVITY AND PHYSICAL-PROPERTIES OF LEAVING GROUPS AND SUBSTRATES [J].

BARTOLI, G ;

TODESCO, PE .

ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (04) :125-132

[9] Tandem nucleophilic addition/cyclization reaction in the synthesis of ketimine-type iminosugars [J].

Behr, Jean-Bernard ;

Kalla, Adel ;

Harakat, Dominique ;

Plantier-Royon, Richard .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3612-3615

[10] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

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