A new synthesis of 3-alkyl-1-isoindolinones

被引:46
作者
Wang, EC [1 ]
Chen, HF [1 ]
Feng, PK [1 ]
Lin, YL [1 ]
Hsu, MK [1 ]
机构
[1] Kaohsiung Med Univ, Sch Chem, Kaohsiung 807, Taiwan
关键词
D O I
10.1016/S0040-4039(02)02273-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new, concise, and efficient method for the synthesis of 3-alkyl-1-isoindolinones was described. 3-Alkyl-3-hydroxy-2,3-dihydro-1-isoindolinones, prepared from the reaction of phthalimide and alkyl lithium, were treated with sodium cyanoborohydride in acidic medium to concomitantly undergo dehydration and reduction leading to various 3-alkyl-1-isoindolinones in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9163 / 9165
页数:3
相关论文
共 17 条
  • [1] A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives
    Allin, SM
    Northfield, CJ
    Page, MI
    Slawin, AMZ
    [J]. TETRAHEDRON LETTERS, 1999, 40 (01) : 143 - 146
  • [2] 1-OXOISOINDOLE CATIONS
    ARMAREGO, WL
    SCHARMA, SC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (11): : 1600 - &
  • [3] Isoindolinone enantiomers having affinity for the dopamine D4 receptor
    Belliotti, TR
    Brink, WA
    Kesten, SR
    Rubin, JR
    Wustrow, DJ
    Zoski, KT
    Whetzel, SZ
    Corbin, AE
    Pugsley, TA
    Heffner, TG
    Wise, LD
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (12) : 1499 - 1502
  • [4] Structure-activity relationships in a series of bisquaternary bisphthalimidine derivatives modulating the muscarinic M2-receptor allosterically
    Cid, HMB
    Tränkle, C
    Baumann, K
    Pick, R
    Mies-Klomfass, E
    Kostenis, E
    Mohr, K
    Holzgrabe, U
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (11) : 2155 - 2164
  • [5] Synthesis of 3-alkyl-1-isoindolinones by alkylation of a benzotriazolyl substituted N-dimethylamino-phthalimidine
    Deniau, E
    Enders, D
    [J]. TETRAHEDRON, 2001, 57 (13) : 2581 - 2588
  • [6] A new simple and convenient synthesis of 3-substituted phthalimidines
    Deniau, E
    Enders, D
    [J]. TETRAHEDRON LETTERS, 2000, 41 (14) : 2347 - 2350
  • [7] PREPARATION OF 11-ARYL-11H-ISOINDOLO[2,1-A]BENZIMIDAZOL-11-OLS
    EBERLE, MK
    HOULIHAN, WJ
    SCHIRM, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (22) : 3872 - 3874
  • [8] HETEROATOM-DIRECTED METALATION - LITHIATION OF N-PROPENYLBENZAMIDES AND N-PROPENYL-ORTHO-TOLUAMIDES - NOVEL ROUTES TO ORTHO-SUBSTITUTED PRIMARY BENZAMIDE DERIVATIVES AND N-UNSUBSTITUTED ISOQUINOLIN-1(2H)-ONES
    FISHER, LE
    MUCHOWSKI, JM
    CLARK, RD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) : 2700 - 2705
  • [9] Novel heterocyclic ring-expansion and/or dehydration-hydration reactions of propargylic and allenylic hydroxy γ-lactams in the presence of strong base or Lewis acid
    Jeong, IY
    Lee, WS
    Goto, S
    Sano, S
    Shiro, M
    Nagao, Y
    [J]. TETRAHEDRON, 1998, 54 (48) : 14437 - 14454
  • [10] Palladium catalyzed cyclization reactions of acetylenic lactams
    Karstens, WFJ
    Stol, M
    Rutjes, FPJT
    Kooijman, H
    Spek, AL
    Hiemstra, H
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 244 - 258