Diversity-oriented synthesis of functionalized Quinolin-2(1H)-ones via pd-catalyzed site-selective cross-coupling reactions

被引：46

作者：

Wang, Zhiyong

Wang, Bing

Wu, He

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2007年 / 9卷 / 05期

关键词：

D O I：

10.1021/cc7000937

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Biologically active 3-amino-4-arylquinolin-2(1H)-ones and 3-alkenyl-4-arylquinolin-2(1H)-ones were synthesized in an efficient and concise manner, utilizing readily available 4-hydroxyquinolin-2(1H)-one as starting material. The key steps, which introduced selectivity and diversity in the synthesis, were the palladium-catalyzed site-selective Suzuki-Miyaura/Buchwald-Hartwig amination and Suzuki-Miyaura/Heck coupling reactions of 3-bromo-4-trifloxy-quinolin-2(1H)-one.

引用

页码：811 / 817

页数：7

共 31 条

[1] Streamlined processes for the synthesis of a farnesyl transferase inhibitor drug candidate [J].

Andresen, BM ;

Couturier, M ;

Cronin, B ;

D'Occhio, M ;

Ewing, MD ;

Guinn, M ;

Hawkins, JM ;

Jasys, VJ ;

LaGreca, SD ;

Lyssikatos, JP ;

Moraski, G ;

Ng, K ;

Raggon, JW ;

Stewart, AM ;

Tickner, DL ;

Tucker, JL ;

Urban, FJ ;

Vazquez, E ;

Wei, LL .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (04) :643-650

[2] Synthesis routes towards the farnesyl protein transferase inhibitor ZARNESTRA™ [J].

Angibaud, PR ;

Venet, MG ;

Filliers, W ;

Broeckx, R ;

Ligny, YA ;

Muller, P ;

Poncelet, VS ;

End, DW .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (03) :479-486

[3]

BEIER N, 1994, HETEROCYCLES, V39, P117

[4] 3-Thio-quinolinone maxi-K openers for the treatment of erectile dysfunction [J].

Boy, KM ;

Guernon, JM ;

Sit, SY ;

Xie, K ;

Hewawasam, P ;

Boissard, CG ;

Dworetzky, SI ;

Natale, J ;

Gribkoff, VK ;

Lodge, N ;

Starrett, JE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (20) :5089-5093

[5] Design, synthesis, structural studies, biological evaluation, and computational simulations of novel potent AT1 angiotensin II receptor antagonists based on the 4-phenylquinoline structure [J].

Cappelli, A ;

Mohr, GL ;

Gallelli, A ;

Rizzo, M ;

Anzini, M ;

Vomero, S ;

Mennuni, L ;

Ferrari, F ;

Makovec, F ;

Menziani, MC ;

De Benedetti, PG ;

Giorgi, G .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (10) :2574-2586

[6] Angiogenesis in cancer and other diseases [J].

Carmeliet, P ;

Jain, RK .

NATURE, 2000, 407 (6801) :249-257

[7] Efficient syntheses of KDR kinase inhibitors using a Pd-catalyzed tandem C-N/Suzuki coupling as the key step [J].

Fang, Yuan-Qing ;

Karisch, Robert ;

Lautens, Mark .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1341-1346

[8]

FERRER P, 1995, LIEBIGS ANN, P1895

[9] Optimization of the indolyl quinolinone class of KDR (VEGFR-2) kinase inhibitors: effects of 5-amido- and 5-sulphonamido-indolyl groups on pharmacokinetics and hERG binding [J].

Fraley, ME ;

Arrington, KL ;

Buser, CA ;

Ciecko, PA ;

Coll, KE ;

Fernandes, C ;

Hartman, GD ;

Hoffman, WF ;

Lynch, JJ ;

McFall, RC ;

Rickert, K ;

Singh, R ;

Smith, S ;

Thomas, KA ;

Wong, BK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) :351-355

[10] Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties. 2. [J].

Freeman, GA ;

Andrews, CW ;

Hopkins, AL ;

Lowell, GS ;

Schaller, LT ;

Cowan, JR ;

Gonzales, SS ;

Koszalka, GW ;

Hazen, RJ ;

Boone, LR ;

Ferris, RG ;

Creech, KL ;

Roberts, GB ;

Short, SA ;

Weaver, K ;

Reynolds, DJ ;

Milton, J ;

Ren, JS ;

Stuart, DI ;

Stammers, DK ;

Chan, JH .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) :5923-5936

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