A mild, one-pot synthesis of 4-quinolones via sequential pd-catalyzed amidation and base-promoted cyclization

被引：99

作者：

Huang, Jinkun ^{[1
]}

Chen, Ying ^{[1
]}

King, Anthony O. ^{[1
]}

Dilmeghani, Mina ^{[1
]}

Larsen, Robert D. ^{[1
]}

Faul, Margaret M. ^{[1
]}

机构：

[1] Amgen Inc, Chem Proc R&D, Thousand Oaks, CA 91320 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 12期

关键词：

D O I：

10.1021/ol800837z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, one-pot synthesis of 4-quinolones is described. Under the optimal conditions, a variety of 2-substituted 4-quinolones were synthesized via sequential palladium-catalyzed amidation of 2'-bromoacetophenones followed by base-promoted intramolecular cyclization.

引用

页码：2609 / 2612

页数：4

共 29 条

[1]

Andriole V., 1988, QUINOLONES

[2]

[Anonymous], J LIEBIGS ANN CHEM

[3] Palladium-catalyzed reaction of aryl halides with ureas [J].

Artamkina, GA ;

Sergeev, AG ;

Beletskaya, IP .

TETRAHEDRON LETTERS, 2001, 42 (26) :4381-4384

[4]

Camps R., 1899, Berichte der Dtsch. Chem. Gesellschaft, V32, P3228, DOI 10.1002/cber.18990320389

[5] CHIMANINES, NEW 2-SUBSTITUTED QUINOLINES, ISOLATED FROM AN ANTIPARASITIC PLANT IN BOLIVIA - GALIPEA-LONGIFLORA [J].

FOURNET, A ;

HOCQUEMILLER, R ;

ROBLOT, F ;

CAVE, A ;

RICHOMME, P ;

BRUNETON, J .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (09) :1547-1552

[6] Organometallic chemistry of amidate complexes.: Accelerating effect of bidentate ligands on the reductive elimination of N-aryl amidates from palladium(II) [J].

Fujita, Ken-ichi ;

Yamashita, Makoto ;

Puschmann, Florian ;

Alvarez-Falcon, Miguel Martinez ;

Incarvito, Christopher D. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) :9044-9045

[7] Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions [J].

Huang, XH ;

Anderson, KW ;

Zim, D ;

Jiang, L ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6653-6655

[8] Pd-catalyzed amidations of aryl chlorides using monodentate biaryl phosphine ligands: A kinetic, computational, and synthetic investigation [J].

Ikawa, Takashi ;

Barder, Timothy E. ;

Biscoe, Mark R. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) :13001-13007

[9] Copper-catalyzed coupling of amides and carbamates with vinyl halides [J].

Jiang, L ;

Job, GE ;

Klapars, A ;

Buchwald, SL .

ORGANIC LETTERS, 2003, 5 (20) :3667-3669

[10] Sequential Cu-catalyzed amidation-base-mediated camps cyclization:: A two-step synthesis of 2-aryl-4-quinolones from o-halophenones [J].

Jones, Carrie P. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :7968-7973

← 1 2 3 →