A straightforward, one-pot protocol for the preparation of libraries of 2-oxazolines

被引：23

作者：

Crosignani, S ^{[1
]}

Swinnen, D ^{[1
]}

机构：

[1] Serono Pharmaceut Res Inst, CH-1228 Geneva, Switzerland

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/cc050011u

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A practical protocol for the parallel synthesis of 2-oxazolines using polymer- supported reagents is described. Polymer-supported Mukaiyama reagent is used to couple a carboxylic acid with an amino alcohol, giving a beta-hydroxyamide, which is then cyclized in situ using either polymer- supported sulfonyl chloride resin or polymer-bound 2-fluoropyridinium triflate. Both 2,4-disubstituted and 2,4,5-trisubstituted 2-oxazolines are obtained in high yields and excellent purities after a simple resin filtration and solvent evaporation routine.

引用

页码：688 / 696

页数：9

共 14 条

[1] Direct synthesis of 2-oxazolines from carboxylic acids using 2-chloro-4,6-dimethoxy-1,3,5-triazine under mild conditions [J].

Bandgar, BP ;

Pandit, SS .

TETRAHEDRON LETTERS, 2003, 44 (11) :2331-2333

[2] Significance of asymmetric sites in choosing siderophores as deferration agents [J].

Bergeron, RJ ;

Xin, MG ;

Weimar, WR ;

Smith, RE ;

Wiegand, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (15) :2469-2478

[3] An enantioselective synthesis of insecticidal 4-alkynyloxazolines [J].

Clark, D ;

Travis, DA .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (11) :2857-2862

[4] Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide [J].

Crosignani, S ;

Young, AC ;

Linclau, B .

TETRAHEDRON LETTERS, 2004, 45 (52) :9611-9615

[5] Polymer-supported mukaiyama reagent: A useful coupling reagent for the synthesis of esters and amides [J].

Crosignani, S ;

Gonzalez, J ;

Swinnen, D .

ORGANIC LETTERS, 2004, 6 (24) :4579-4582

[6]

HAHN BH, 1981, J RHEUMATOL, V8, P783

[7] Synthesis and biological evaluation of 2-indolyloxazolines as a new class of tubulin polymerization inhibitors. Discovery of A-289099 as an orally active antitumor agent [J].

Li, Q ;

Woods, KW ;

Claiborne, A ;

Gwaltney, SL ;

Barr, KJ ;

Liu, G ;

Gehrke, L ;

Credo, RB ;

Hui, YH ;

Lee, J ;

Warner, RB ;

Kovar, P ;

Nukkala, MA ;

Zielinski, NA ;

Tahir, SK ;

Fitzgerald, M ;

Kim, KH ;

Marsh, K ;

Frost, D ;

Ng, SC ;

Rosenberg, S ;

Sham, HL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (03) :465-469

[8]

OBATA T, 1995, Patent No. 655444

[9] Antibacterial agents that inhibit lipid A biosynthesis [J].

Onishi, HR ;

Pelak, BA ;

Gerckens, LS ;

Silver, LL ;

Kahan, FM ;

Chen, MH ;

Patchett, AA ;

Galloway, SM ;

Hyland, SA ;

Anderson, MS ;

Raetz, CRH .

SCIENCE, 1996, 274 (5289) :980-982

[10] Synthesis of functionalized oxazolines and oxazoles with DAST and deoxo-fluor [J].

Phillips, AJ ;

Uto, Y ;

Wipf, P ;

Reno, MJ ;

Williams, DR .

ORGANIC LETTERS, 2000, 2 (08) :1165-1168

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