Isocyanide Insertion: De Novo Synthesis of Trifluoromethylated Phenanthridine Derivatives

被引：127

作者：

Cheng, Yuanzheng

Jiang, Heng

Zhang, Yan

Yu, Shouyun ^{[1
]}

机构：

[1] Nanjing Univ, State Key Lab Analyt Chem Life Sci, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 21期

基金：

中国国家自然科学基金;

关键词：

OXIDATIVE CYCLIZATION; FLUORINE; ARYLATION; PYRIDINE; 6-(TRIFLUOROMETHYL)PHENANTHRIDINES; 2-ISOCYANOBIPHENYLS; HETEROARENES; INHIBITORS; ALKALOIDS; CATALYSIS;

D O I：

10.1021/ol4026827

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mechanistically new strategy has been described for the simple, practical, and environmentally friendly preparation of 6-(trifluoromethyl)phenanthridine derivatives using ionic isocyanide insertion from biphenyl isocyanide derivatives and Umemoto's reagent. These reactions were promoted only by inorganic base in good-to-excellent chemical yields without any external stoichiometric oxidants and radical initiators.

引用

页码：5520 / 5523

页数：4

共 70 条

[1]

Abdel-Halim O. B., 2004, NAT PROD, V67, P7

[2]

[Anonymous], 2009, Angew. Chem

[3] Elemental fluorine. Part 10. Selective fluorination of pyridine, quinoline and quinoxaline derivatives with fluorine-iodine mixtures [J].

Chambers, RD ;

Parsons, M ;

Sandford, G ;

Skinner, CJ ;

Atherton, MJ ;

Moilliet, JS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (07) :803-810

[4]

Chiba S., 2010, ORG LETT, V12, P9

[5]

Chu L., 2010, ORG LETT, V12, P21

[6] LEWIS-ACID CATALYZED CYCLIZATION AND HALOGEN EXCHANGE-REACTIONS OF 1,1'-BIPHENYL-2-YL ISOCYANIDE DIHALIDES [J].

CURRIE, KS ;

TENNANT, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (22) :2295-2296

[7] Electrolytic fluorination of organic compounds [J].

Dawood, KM .

TETRAHEDRON, 2004, 60 (07) :1435-1451

[8] Chiral Calcium Organophosphate-Catalyzed Enantioselective Electrophilic Amination of Enamides [J].

Drouet, Fleur ;

Lalli, Claudia ;

Liu, Hua ;

Masson, Geraldine ;

Zhu, Jieping .

ORGANIC LETTERS, 2011, 13 (01) :94-97

[9] INHIBITORS OF DNA TOPOISOMERASE-I ISOLATED FROM THE ROOTS OF ZANTHOXYLUM-NITIDUM [J].

FANG, SD ;

WANG, LK ;

HECHT, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5025-5027

[10] In Vitro Leishmanicidal Activity of Benzophenanthridine Alkaloids from Bocconia pearcei and Related Compounds [J].

Fuchino, Hiroyuki ;

Kawano, Marii ;

Mori-Yasumoto, Kanami ;

Sekita, Setsuko ;

Satake, Motoyoshi ;

Ishikawa, Tsutomu ;

Kiuchi, Fumiyuki ;

Kawahara, Nobuo .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (08) :1047-1050

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