Cobalt-catalyzed intramolecular C-N and C-O cross-coupling reactions: synthesis of benzimidazoles and benzoxazoles

被引：124

作者：

Saha, Prasenjit ^{[1
]}

Ali, Md Ashif ^{[1
]}

Ghosh, Pokhraj ^{[1
]}

Punniyamurthy, Tharmalingam ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 24期

关键词：

EFFICIENT HETEROGENEOUS CATALYST; II RECEPTOR ANTAGONISTS; ARYL GRIGNARD-REAGENTS; BOND FORMATION; 2-ARYLBENZIMIDAZOLE DERIVATIVES; BIOLOGICAL EVALUATION; ACTIVATED CARBON; IN-VITRO; COPPER; HALIDES;

D O I：

10.1039/c0ob00405g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cobalt(II)-complex catalyzes efficiently the intramolecular C-N and C-O cross-couplings of Z-N'-(2-halophenyl)-N-phenylamidines and N-(2-bromophenyl)benzamides to afford the corresponding substituted benzimidazoles and benzoxazoles in the presence of K2CO3 at moderate temperature. The protocol is general, air stable and affords the products selectively in moderate to high yield.

引用

页码：5692 / 5699

页数：8

共 87 条

[1] Efficient Copper-Catalyzed N-Arylation of Amides and Imidazoles with Aryl Iodides [J].

Ali, Md. Ashif ;

Saha, Prasenjit ;

Punniyamurthy, Tharmalingam .

SYNTHESIS-STUTTGART, 2010, (06) :908-910

[2] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles [J].

Altenhoff, G ;

Glorius, F .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1661-1664

[3] Electron-transfer reorganization energies of isolated organic molecules [J].

Amashukeli, X ;

Winkler, JR ;

Gray, HB ;

Gruhn, NE ;

Lichtenberger, DL .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (33) :7593-7598

[4] Efficient cobalt-catalyzed formation of unsymmetrical biaryl compounds and its application in the synthesis of a sartan intermediate [J].

Amatore, Muriel ;

Gosmini, Corinne .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2089-2092

[5] Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides:: a straightforward approach to benzo[d]oxazoles in water [J].

Barbero, Nekane ;

Carril, Monica ;

SanMartin, Raul ;

Dominguez, Esther .

TETRAHEDRON, 2007, 63 (42) :10425-10432

[6] Telmisartan - A review of its use in the management of hypertension [J].

Battershill, AJ ;

Scott, LJ .

DRUGS, 2006, 66 (01) :51-83

[7] Cobalt-Catalyzed Cross-Coupling Between In Situ Prepared Arylzinc Halides and 2-Chloropyrimidine or 2-Chloropyrazine [J].

Begouin, Jeanne-Marie ;

Gosmini, Corinne .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08) :3221-3224

[8] Highly efficient nickel-catalyzed cross-coupling of succinic and glutaric anhydrides with organozinc reagents [J].

Bercot, EA ;

Rovis, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :247-254

[9] MEMORY EFFECTS AND 1,3-DIAZEPINE RING-CLOSURE IN ARYLNITRENIUM IONS [J].

BINDING, N ;

HEESING, A .

CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (05) :1822-1833

[10] Oxidative conversion of amines into benzoxazoles using hydrogen transfer catalysis [J].

Blacker, A. John ;

Farah, Mohamed M. ;

Marsden, Stephen P. ;

Saidi, Ourida ;

Williams, Jonathan M. J. .

TETRAHEDRON LETTERS, 2009, 50 (45) :6106-6109

← 1 2 3 4 5 6 7 8 9 →