Catalytic amination of 2-substituted pyridines with hydrazine derivatives

被引：86

作者：

Arterburn, JB ^{[1
]}

Rao, KV ^{[1
]}

Ramdas, R ^{[1
]}

Dible, BR ^{[1
]}

机构：

[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 09期

关键词：

D O I：

10.1021/ol015731y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Protected pyridylhydrazine derivatives were prepared in a one-step palladium-catalyzed amination reaction using chelating phosphine ligands, 2-Pyridyl chlorides, bromides, and triflates were effective electrophiles in these reactions, Di-tert-butyl hydrazodiformate was an excellent hydrazine substrate, and the resulting products were deprotected under mild conditions. Catalytic amination provides a direct route to protected bifunctional hydrazinopyridine linkers that are suitable for metal-bioconjugate syntheses.

引用

页码：1351 / 1354

页数：4

共 52 条

[1]

ABRAMS MJ, 1990, J NUCL MED, V31, P2022

[2] First application of fac-[99mTc(OH2)3(CO)3]+ in bioorganometallic chemistry:: Design, structure, and in vitro affinity of a 5-HT1A receptor ligand labeled with 99mTc [J].

Alberto, R ;

Schibli, R ;

Schubiger, AP ;

Abram, U ;

Pietzsch, HJ ;

Johannsen, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (25) :6076-6077

[3] Mechanistic studies of the palladium-catalyzed amination of aryl halides and the oxidative addition of aryl bromides to Pd(BINAP)2 and Pd(DPPF)2:: An unusual case of zero-order kinetic behavior and product inhibition [J].

Alcazar-Roman, LM ;

Hartwig, JF ;

Rheingold, AL ;

Liable-Sands, LM ;

Guzei, IA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4618-4630

[4] DESIGN, SYNTHESIS, AND PHARMACOLOGICAL ACTIVITIES OF 2-SUBSTITUTED 4-PHENYLQUINOLINES AS POTENTIAL ANTIDEPRESSANT DRUGS [J].

ALHAIDER, AA ;

ABDELKADER, MA ;

LIEN, EJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (10) :1394-1398

[5] Functionalized organoimidorhenium(v) complexes as potential radiopharmaceuticals: Syntheses of glycine derivatives and the structure determination of a rhenium analogue of chlorambucil [J].

Arterburn, JB ;

Fogarty, IM ;

Hall, KA ;

Ott, KC ;

Bryan, JC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (23-24) :2877-2879

[6]

Arterburn JB, 2000, ANGEW CHEM INT EDIT, V39, P771, DOI 10.1002/(SICI)1521-3773(20000218)39:4<771::AID-ANIE771>3.3.CO

[7]

2-5

[8] Functionalized rhenium(V) organoimido complexes as potential radiopharmaceuticals.: 2.: Synthesis, structural characterization, and reactivity of N-succinimidyl ester derivatives with amines [J].

Arterburn, JB ;

Rao, KV ;

Goreham, DM ;

Valenzuela, MV ;

Holguin, MS ;

Hall, KA ;

Ott, KC ;

Bryan, JC .

ORGANOMETALLICS, 2000, 19 (09) :1789-1795

[9] Recent synthetic advances in the nucleophilic amination of benzenes [J].

Belfield, AJ ;

Brown, GR ;

Foubister, AJ .

TETRAHEDRON, 1999, 55 (38) :11399-11428

[10] Nickel-mediated amination chemistry.: Part 2:: Selective N-arylation or N,N′-diarylation of piperazine [J].

Brenner, E ;

Schneider, R ;

Fort, Y .

TETRAHEDRON LETTERS, 2000, 41 (16) :2881-2884

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