Synthesis of piperazinones and benzopiperazinones from 1,2-diamines and organoboronic acids

被引:73
作者
Petasis, NA [1 ]
Patel, ZD
机构
[1] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA
[2] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)01717-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkenyl, aryl and heteroaryl boronic acids react with 1,2-diamines and glyoxylic acid to give directly in one step the corresponding piperazinones (2-oxopiperazines). Similarly, the use of monoprotected 1,2-phenylenediamine leads to benzopiperazinones( 1,2,3,4-tetrahydroquinoxalin-2-ones). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9607 / 9611
页数:5
相关论文
共 24 条
  • [1] ABELL A, 1999, ADV AMINO ACID MIMET, V2, P1
  • [2] Molecular recognition of protein-ligand complexes: Applications to drug design
    Babine, RE
    Bender, SL
    [J]. CHEMICAL REVIEWS, 1997, 97 (05) : 1359 - 1472
  • [3] Efficient synthesis of substituted piperazinones via tandem reductive amination-cyclization
    Dinsmore, CJ
    Zartman, CB
    [J]. TETRAHEDRON LETTERS, 2000, 41 (33) : 6309 - 6312
  • [4] Recent advances in the preparation of heterocycles on solid support:: A review of the literature
    Franzén, RG
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (03): : 195 - 214
  • [5] A peptoid based synthesis of di- and tri-substituted 2-oxopiperazines on solid support
    Goff, DA
    [J]. TETRAHEDRON LETTERS, 1998, 39 (12) : 1473 - 1476
  • [6] Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics
    Hanessian, S
    McNaughtonSmith, G
    Lombart, HG
    Lubell, WD
    [J]. TETRAHEDRON, 1997, 53 (38) : 12789 - 12854
  • [7] Synthesis of piperazinones and their application in constrained mimetics of the growth hormone secretagogue NN703
    Hansen, TK
    Schlienger, N
    Hansen, BS
    Andersen, PH
    Bryce, MR
    [J]. TETRAHEDRON LETTERS, 1999, 40 (18) : 3651 - 3654
  • [8] Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy
    Hulme, C
    Peng, J
    Louridas, B
    Menard, P
    Krolikowski, P
    Kumar, NV
    [J]. TETRAHEDRON LETTERS, 1998, 39 (44) : 8047 - 8050
  • [9] 3,4,5-trifluorobenzeneboronic acid as an extremely active amidation catalyst
    Ishihara, K
    Ohara, S
    Yamamoto, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) : 4196 - 4197
  • [10] Ishihara K, 1999, EUR J ORG CHEM, V1999, P527