Efficient synthesis of N-arylpiperazinones via a selective intramolecular Mitsunobu cyclodehydration

被引:25
作者
Weissman, SA [1 ]
Lewis, S [1 ]
Askin, D [1 ]
Volante, RP [1 ]
Reider, PJ [1 ]
机构
[1] Merck & Co Inc, Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1016/S0040-4039(98)01670-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical two pot synthesis of N-arylpiperazinones from the corresponding aniline is described. The key transformation is a selective intramolecular Mitsunobu cyclodehydration of an amidoalcohol intermediate. A series of N-arylpiperazinones were prepared in yields up to 89%. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7459 / 7462
页数:4
相关论文
共 20 条
  • [1] ARCHER S, 1968, Patent No. 3365453
  • [2] A synthesis of monoketopiperazines
    Aspinall, SR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 : 1202 - 1204
  • [3] NOVEL CHOLECYSTOKININ RECEPTOR LIGANDS OXOPIPERAZINES DERIVED FROM BOC-CCK-4
    BATT, AR
    KENDRICK, DA
    MATHEWS, E
    ROOKER, DP
    RYDER, H
    SEMPLE, G
    SZELKE, M
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (07) : 867 - 872
  • [4] CACCIA S, 1985, BIOCHEM PHARMACOL, V34, P39
  • [5] COSSEC B, 1989, PHARMAZIE, V44, P643
  • [6] An unexpected Mitsunobu reaction. A direct route to the 2,5-diazabicyclo[2.2.1]heptan-3-one skeleton as a gamma-lactam mimic of beta-lactam antibiotics
    Hadfield, PS
    Galt, RHB
    Sawyer, Y
    Layland, NJ
    Page, MI
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 503 - 509
  • [7] Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]
  • [8] Progress in the Mitsunobu reaction. A review
    Hughes, DL
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (02) : 127 - 164
  • [9] LACTAM AND AMIDE ACETALS .21. USE OF PYROGLUTAMIC ACID AND PROLINE IN CHIRAL SYNTHESIS OF CONFORMATIONALLY CONSTRAINED PIPERAZINONES
    JAIN, S
    SUJATHA, K
    KRISHNA, KVR
    ROY, R
    SINGH, J
    ANAND, N
    [J]. TETRAHEDRON, 1992, 48 (23) : 4985 - 4998
  • [10] TRYPTOPHAN-DERIVED NK1 ANTAGONISTS - CONFORMATIONALLY CONSTRAINED HETEROCYCLIC BIOISOSTERES OF THE ESTER LINKAGE
    LEWIS, RT
    MACLEOD, AM
    MERCHANT, KJ
    KELLEHER, F
    SANDERSON, I
    HERBERT, RH
    CASCIERI, MA
    SADOWSKI, S
    BALL, RG
    HOOGSTEEN, K
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (06) : 923 - 933