Synthesis of Substituted Pyrazoles via Tandem Cross-Coupling/Electrocyclization of Enol Triflates and Diazoacetates

被引：71

作者：

Babinski, David J. ^{[1
]}

Aguilar, Hector R. ^{[1
]}

Still, Raymond ^{[1
]}

Frantz, Doug E. ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 15期

关键词：

ELECTROCYCLIZATION ENANTIOSELECTIVE SYNTHESIS; DIAZO-COMPOUNDS; CYCLOADDITION; LIGANDS; CYCLIZATION; INHIBITORS; BEHAVIOR;

D O I：

10.1021/jo201042c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 3,4,5-trisubstituted pyrazoles via a tandem catalytic cross-coupling/electrocydization of enol triflates and diazoacetates is presented. The initial scope of this methodology is demonstrated on a range of differentially substituted acyclic and cyclic enol triflates as well as an elaborated set of diazoacetates to provide the corresponding pyrazoles with a high degree of structural complexity.

引用

页码：5915 / 5923

页数：9

共 50 条

[11] Tandem 6π-Electrocyclization and Cycloaddition of Nitrodienes to Yield Multicyclic Nitroso Acetals [J].

Creech, Gardner S. ;

Kwon, Ohyun .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) :8876-+

[12] Synthesis of pyrazole-3-carboxylates and pyrazole-1,5-dicarboxylates by one-pot cyclization of hydrazone dianions with diethyl oxalate [J].

Dang, Tung T. ;

Dang, Tuan T. ;

Fischer, Christine ;

Goerls, Helmar ;

Langer, Peter .

TETRAHEDRON, 2008, 64 (09) :2207-2215

[13] ALPHA-HYDROXY ESTERS AS CHIRAL AUXILIARIES IN ASYMMETRIC CYCLOPROPANATIONS BY RHODIUM(II)-STABILIZED VINYLCARBENOIDS [J].

DAVIES, HML ;

HUBY, NJS ;

CANTRELL, WR ;

OLIVE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9468-9479

[14] Synthesis of Fully Substituted Pyrazoles via Regio- and Chemoselective Metalations [J].

Despotopoulou, Christina ;

Klier, Lydia ;

Knochel, Paul .

ORGANIC LETTERS, 2009, 11 (15) :3326-3329

[15] Effective and highly stereoselective coupling with vinyldiazomethanes to form symmetrical trienes [J].

Doyle, MP ;

Yan, M .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :602-604

[16]

Elguero J., 1996, In Comprehensive Heterocyclic Chemistry II, V3

[17] Dinuclear Allylpalladium Complexes of C2-Symmetric Pyrazolate-Bridged Bis(oxazoline) Ligands (pyrbox's): Structures, Dynamic Behavior, and Application in Asymmetric Allyllic Alkylation [J].

Ficks, Arne ;

Sibbald, Connor ;

John, Michael ;

Dechert, Sebastian ;

Meyer, Franc .

ORGANOMETALLICS, 2010, 29 (05) :1117-1126

[18] C-H Bonds as Ubiquitous Functionality: A General Approach to Complex Arylated Pyrazoles via Sequential Regioselective C-Arylation and N-Alkylation Enabled by SEM-Group Transposition [J].

Goikhman, Roman ;

Jacques, Teresa L. ;

Sames, Dalibor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (08) :3042-3048

[19] REACTIONS OF DIAZOKETONES .9. ADDITION OF DIAZOKETONES TO BETA-DICARBONYLCOMPOUNDS [J].

HAMPEL, W .

JOURNAL FUR PRAKTISCHE CHEMIE, 1969, 311 (06) :1058-&

[20] Parallel synthesis of potent, pyrazole-based inhibitors of Helicobacter pylori dihydroorotate dehydrogenase [J].

Haque, TS ;

Tadesse, S ;

Marcinkeviciene, J ;

Rogers, MJ ;

Sizemore, C ;

Kopcho, LM ;

Amsler, K ;

Ecret, LD ;

Zhan, DL ;

Hobbs, F ;

Slee, A ;

Trainor, GL ;

Stern, AM ;

Copeland, RA ;

Combs, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (21) :4669-4678

← 1 2 3 4 5 →