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

被引：137

作者：

Banwell, MG ^{[1
]}

Lupton, DW ^{[1
]}

Ma, XH ^{[1
]}

Renner, J ^{[1
]}

Sydnes, MO ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 16期

关键词：

D O I：

10.1021/ol0490375

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of beta-halo-enals, -enones, or -esters readily affords the corresponding beta-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.

引用

页码：2741 / 2744

页数：4

共 44 条

[31] A mild and efficient one-step synthesis of quinolines [J].

McNaughton, BR ;

Miller, BL .

ORGANIC LETTERS, 2003, 5 (23) :4257-4259

[32] Unprecedented hydrothermal reaction of O-phenylaniline and related derivatives with cyclic ketones.: A novel approach to the construction of phenanthridine and quinoline ring systems [J].

Mehta, BK ;

Yanagisawa, K ;

Shiro, M ;

Kotsuki, H .

ORGANIC LETTERS, 2003, 5 (10) :1605-1608

[33] Quinoline, quinazoline and acridone alkaloids [J].

Michael, JP .

NATURAL PRODUCT REPORTS, 2002, 19 (06) :742-760

[34]

MIGACHEV GI, 1981, KHIM GETEROTSIKL+, P388

[35] INTRAMOLECULAR TRAPPING OF HYDROXYLAMINES FROM CATALYTIC HYDROGENATION OF 2-NITROBIPHENYLS [J].

MUTH, CW ;

ELKINS, JR ;

DEMATTE, ML ;

CHIANG, ST .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (04) :1106-&

[36]

Nelson T. D., 2004, ORG REACT, P265

[37] MOLECULAR DESIGN AND CHEMICAL SYNTHESIS OF POTENT ENEDIYNES .2. DYNEMICIN MODEL SYSTEMS EQUIPPED WITH C-3 TRIGGERING DEVICES AND EVIDENCE FOR QUINONE METHIDE FORMATION IN THE MECHANISM OF ACTION OF DYNEMICIN-A [J].

NICOLAOU, KC ;

DAI, WM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8908-8921

[38] Ionic liquid-promoted regiospecific Friedlander annulation: Novel synthesis of quinolines and fused polycyclic quinolines [J].

Palimkar, SS ;

Siddiqui, SA ;

Daniel, T ;

Lahoti, RJ ;

Srinivasan, KV .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9371-9378

[39] SYNTHESIS OF BETA-CHLORO, BETA-BROMO, AND BETA-IODO ALPHA,BETA-UNSATURATED KETONES [J].

PIERS, E ;

GRIERSON, JR ;

LAU, CK ;

NAGAKURA, I .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (02) :210-223

[40] Iodine(III)-mediated generation of nitrogen-tethered orthoquinol acetates for the construction of oxygenated indole, quinoline, and phenanthridine alkaloid motifs [J].

Pouységu, L ;

Avellan, AV ;

Quideau, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3425-3436

← 1 2 3 4 5 →