Toward safer methodologies for the synthesis of polyheterocyclic systems:: intramolecular arylation of arenes under Mizoroki-Heck reaction conditions

被引：50

作者：

Hernández, S ^{[1
]}

SanMartin, R ^{[1
]}

Tellitu, I ^{[1
]}

Domínguez, E ^{[1
]}

机构：

[1] Euskal Herriko Unibertsitatea, Kimika Organikoa Saila 2, Zientzi Fak, Bilbao 48080, Spain

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 07期

关键词：

D O I：

10.1021/ol034148+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] A straightforward synthesis of ibudilast-related pyrazolo[1,5-f]phenanthridines is accomplished by a tandem amine-exchange/heterocyclization of arylenaminones followed by an intramolecular biaryl coupling of the so-formed diarylpyrazoles. The direct, environmentally convenient ring-closure of the latter pyrazole intermediates, which show a close resemblance to the antiinflammatory drug celecoxib, is efficiently performed under Mizoroki-Heck reaction conditions.

引用

页码：1095 / 1098

页数：4

共 55 条

[1]

AKAHANE A, 2002, Patent No. 0218382

[2]

ALBERTI MJ, 2002, Patent No. 0278700

[3] Pyrrolo[1,2-f]phenanthridines and related non-rigid analogues as antiviral agents [J].

Almerico, AM ;

Mingoia, F ;

Diana, P ;

Barraja, P ;

Montalbano, A ;

Lauria, A ;

Loddo, R ;

Sanna, L ;

Delpiano, D ;

Setzu, MG ;

Musiu, C .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (01) :3-10

[4] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].

Amatore, C ;

Jutand, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321

[5]

Baguley PA, 1998, ANGEW CHEM INT EDIT, V37, P3073, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3072::AID-ANIE3072>3.0.CO

[6]

2-9

[7] Interactive SAR studies:: Rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists [J].

Bettinetti, L ;

Schlotter, K ;

Hübner, H ;

Gmeiner, P .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (21) :4594-4597

[8] Solution phase combinatorial synthesis of biaryl libraries employing heterogeneous conditions for catalysis and isolation with size exclusion chromatography for purification [J].

Boger, DL ;

Goldberg, J ;

Andersson, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2422-2427

[9] Atropisomerization barriers of configurationally unstable biaryl compounds, useful substrates for atroposelective conversions to axially chiral biaryls [J].

Bringmann, G ;

Heubes, M ;

Breuning, M ;

Göbel, L ;

Ochse, M ;

Schöner, B ;

Schupp, O .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :722-728

[10] The interaction of DNA with intercalating agents probed by sodium-23 NMR relaxation rates [J].

Casu, M ;

Puligheddu, S ;

Saba, G ;

Marincola, FC ;

Orellana, G ;

Lai, A .

JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1997, 15 (01) :37-43

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