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

被引：47

作者：

Brenner, E ^{[1
]}

Schneider, R ^{[1
]}

Fort, Y ^{[1
]}

机构：

[1] Univ Nancy 1, Fac Sci, UMR CNRS UHP 7565, F-54506 Vandoeuvre Nancy, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 16期

关键词：

nickel; arylamination; N-arylpiperazine; N; '-diarylpiperazine;

D O I：

10.1016/S0040-4039(00)00277-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2,2'-bipyridine liganded Ni catalyst has revealed a good selectivity in the mono arylation of piperazine starting from aryl chlorides allowing a selective and efficient synthesis of N-arylpiperazines using stoichiometric amounts of reagents. The preparation of N,N'-diaryl substituted piperazines is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2881 / 2884

页数：4

共 35 条

[11] Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides
Hartwig, JF
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) : 852 - 860
[12] Sequential mono-N-arylation of piperazine nitrogens.: Part 1:: A simplified method and its application to the preparation of a key N,N′-biaryl piperazine antifungal intermediate
Hepperle, M
Eckert, J
Gala, D
[J]. TETRAHEDRON LETTERS, 1999, 40 (31) : 5655 - 5659
[13] Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine
Kerrigan, F
Martin, C
Thomas, GH
[J]. TETRAHEDRON LETTERS, 1998, 39 (15) : 2219 - 2222
[14] Synthesis of new (benzimidazolyl)piperazines with affinity for the 5-HT1a receptor via Pd(0) amination of bromobenzimidazoles
López-Rodriguez, ML
Viso, A
Benhamú, B
Rominguera, JL
Murcia, M
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) : 2339 - 2342
[15] Design and synthesis of 2-[4-[4-(m-(ethylsulfonamido)-phenyl)piperazin-1-yl]butyl]-1,3-dioxoperhydropyrrolo[1,2-c]imidazole (EF-7412) using neural networks.: A selective derivative with mixed 5-HT1A/D2 antagonist properties
López-Rodríguez, ML
Morcillo, MJ
Fernández, E
Rosado, ML
Orensanz, L
Beneytez, ME
Manzanares, J
Fuentes, JA
Schaper, KJ
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (12) : 1679 - 1682
[16] Synthesis and structure-activity relationships of a new model of arylpiperazines .3. 2-[omega-(4-arylpiperazin-1-yl)alkyl]perhydropyrrolo-[1,2-c]imidazoles and -perhydroimidazo[1,5-a]pyridines: Study of the influence of the terminal amide fragment on 5-HT1A affinity/selectivity
LopezRodriguez, ML
Morcillo, MJ
Fernandez, E
Porras, E
Murcia, M
Sanz, AM
Orensanz, L
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (16) : 2653 - 2656
[17] Formation of phenylpiperazines by a novel alumina supported bis-alkylation.
Mishani, E
Dence, CS
McCarthy, TJ
Welch, MJ
[J]. TETRAHEDRON LETTERS, 1996, 37 (03) : 319 - 322
[18] STRUCTURE ACTIVITY RELATIONSHIP STUDIES OF CENTRAL-NERVOUS-SYSTEM AGENTS .5. EFFECT OF THE HYDROCARBON CHAIN ON THE AFFINITY OF 4-SUBSTITUTED 1-(3-CHLOROPHENYL)PIPERAZINES FOR 5-HT1A RECEPTOR-SITE
MOKROSZ, JL
PIETRASIEWICZ, M
DUSZYNSKA, B
CEGLA, MT
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (13) : 2369 - 2374
[19] Practical application of the palladium-catalyzed amination in phenylpiperazine synthesis: An efficient synthesis of a metabolite of the antipsychotic agent aripiprazole
Morita, S
Kitano, K
Matsubara, J
Ohtani, T
Kawano, Y
Otsubo, K
Uchida, M
[J]. TETRAHEDRON, 1998, 54 (19) : 4811 - 4818
[20] Solution phase combinatorial synthesis of arylpiperazines
Neuville, L
Zhu, JP
[J]. TETRAHEDRON LETTERS, 1997, 38 (23) : 4091 - 4094

← 1 2 3 4 →