Phenanthridine Synthesis through Iron-Catalyzed Intramolecular N-Arylation of O-Acetyl Oxime

被引：108

作者：

Deb, Indubhusan ^{[1
]}

Yoshikai, Naohiko ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 16期

基金：

新加坡国家研究基金会;

关键词：

RADICAL CYCLIZATION; BIOLOGICAL-ACTIVITY; DIOXIME OXALATES; IMINYL RADICALS; AROMATIC IMINES; ARYL CHLORIDES; DERIVATIVES; ACTIVATION; REAGENTS; NITROGEN;

D O I：

10.1021/ol4020392

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

O-Acetyl oximes derived from 2'-arylacetophenones undergo N-O bond cleavage/intramolecular N-arylation in the presence of a catalytic amount of iron(III) acetylacetonate in acetic acid. In combination with the conventional cross-coupling or directed C-H arylation, the reaction offers a convenient route to substituted phenanthridines.

引用

页码：4254 / 4257

页数：4

共 30 条

[1] Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (14) :3123-3125

[2] 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

[3] Photochemistry of acyloximes: synthesis of heterocycles and natural products [J].

Alonso, Rafael ;

Caballero, Alegria ;

Campos, Pedro J. ;

Rodriguez, Miguel A. .

TETRAHEDRON, 2010, 66 (46) :8828-8831

[4] Application of Organic Azides for the Synthesis of Nitrogen-Containing Molecules [J].

Chiba, Shunsuke .

SYNLETT, 2012, 23 (01) :21-44

[5] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF STRUCTURAL ANALOGS OF THE ANTICANCER BENZOPHENANTHRIDINE ALKALOID NITIDINE CHLORIDE [J].

CUSHMAN, M ;

MOHAN, P ;

SMITH, ECR .

JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (04) :544-547

[6] Free radical cyclizations involving nitrogen [J].

Fallis, AG ;

Brinza, IM .

TETRAHEDRON, 1997, 53 (52) :17543-17594

[7] 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

[8] Cobalt-Catalyzed Ortho-Arylation of Aromatic Imines with Aryl Chlorides [J].

Gao, Ke ;

Lee, Pin-Sheng ;

Long, Chong ;

Yoshikai, Naohiko .

ORGANIC LETTERS, 2012, 14 (16) :4234-4237

[9] Palladium-Catalyzed Aerobic Dehydrogenative Aromatization of Cyclohexanone Imines to Arylamines [J].

Hajra, Alakananda ;

Wei, Ye ;

Yoshikai, Naohiko .

ORGANIC LETTERS, 2012, 14 (21) :5488-5491

[10] A RuH2(CO)(PPh3)3-catalyzed regioselective arylation of aromatic ketones with arylboronates via carbon-hydrogen bond cleavage [J].

Kakiuchi, F ;

Matsuura, Y ;

Kan, S ;

Chatani, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5936-5945

← 1 2 3 →