Palladium-catalyzed N-heteroannulation of N-allyl- or N-benzyl-2-nitrobenzenamines:: synthesis of 2-substituted benzimidazoles

被引：44

作者：

Hubbard, Jeremiah W. ^{[1
]}

Piegols, Adam M. ^{[1
]}

Soederberg, Bjoern C. G. ^{[1
]}

机构：

[1] W Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA

来源：

TETRAHEDRON | 2007年 / 63卷 / 30期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/j.tet.2007.05.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed reductive N-heteroannulation of N-allyl-or N-benzyl-2-nitrobenzenamines, using carbon monoxide as the ultimate reducing agent, affording 2-substituted benzimidazoles has been developed. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：7077 / 7085

页数：9

共 62 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2] TRANSITION-METAL COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION - SYNTHESIS OF 4(3H)-QUINAZOLINONE DERIVATIVES FROM N-(2-NITROBENZOYL)AMIDES [J].

AKAZOME, M ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :310-312

[3] PALLADIUM COMPLEX-CATALYZED INTERMOLECULAR REDUCTIVE N-HETEROCYCLIZATION - NOVEL SYNTHESIS OF QUINAZOLINE DERIVATIVES FROM 2-NITROBENZALDEHYDE OR 2-NITROPHENYL KETONES WITH FORMAMIDE [J].

AKAZOME, M ;

YAMAMOTO, J ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 494 (1-2) :229-233

[4] PALLADIUM COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF NITROARENES - NOVEL SYNTHESIS OF INDOLE AND 2H-INDAZOLE DERIVATIVES [J].

AKAZOME, M ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3375-3380

[5] AN EFFICIENT SYNTHESIS OF 2-VINYLBENZIMIDAZOLES FROM 1-(2-BENZIMIDAZOL-2-YLETHYL)PYRIDINIUM SALTS USING AN ANION-EXCHANGE RESIN [J].

ALCALDE, E ;

PEREZGARCIA, L ;

DINARES, I ;

FRIGOLA, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6516-6521

[6] 4(1H)-quinolinone alkaloids. An efficient synthesis of graveoline by palladium-catalysed reductive N-heterocyclisation. [J].

Annunziata, R ;

Cenini, S ;

Palmisano, G ;

Tollan, S .

SYNTHETIC COMMUNICATIONS, 1996, 26 (03) :495-501

[7] TRIRUTHENIUM DODECACARBONYL-CATALYZED REDUCTIVE CARBONYLATION OF NITROARENES - CYCLIZATION, CARBON-MONOXIDE INSERTION AND REDUCTION - AN OVERVIEW [J].

BASSOLI, A ;

CENINI, S ;

FARINA, F ;

ORLANDI, M ;

RINDONE, B .

JOURNAL OF MOLECULAR CATALYSIS, 1994, 89 (1-2) :121-142

[8] A ''one-pot'' phase transfer alkylation/hydrolysis of o-nitrotrifluoroacetanilides. A convenient route to N-alkyl o-phenylenediamines [J].

Brown, SA ;

Rizzo, CJ .

SYNTHETIC COMMUNICATIONS, 1996, 26 (21) :4065-4080

[9] Palladium-catalyzed synthesis of 3-alkoxysubstituted indoles [J].

Clawson, Ronald W., Jr. ;

Deavers, Robert E., III ;

Akhmedov, Novruz G. ;

Soderberg, Bjorn C. G. .

TETRAHEDRON, 2006, 62 (47) :10829-10834

[10] PHOTOCYCLISATION OF 1-STYRYLIMIDAZOLES - NOVEL ROUTE TO N-BRIDGEHEAD COMPOUNDS [J].

COOPER, G ;

IRWIN, WJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (01) :75-80

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