Synthesis of 3-alkylideneisoindolinones and isoindolones by a Horner-Wadsworth-Emmons reaction

被引:16
|
作者
Angel Reyes-Gonzalez, Miguel [1 ]
Zamudio-Medina, Angel [1 ]
Abelardo Ramirez-Marroquin, Oscar [1 ]
Ordonez, Mario [1 ]
机构
[1] Univ Autonoma Estado Morelos, Ctr Invest Quim, Cuernavaca, Morelos, Mexico
来源
MONATSHEFTE FUR CHEMIE | 2014年 / 145卷 / 06期
关键词
Phosphonates; Three-component reaction; Wittig reaction; Heterocycles; ISOINDOLINONE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; INHIBITORY-ACTIVITY; POTENT INHIBITORS; CYCLIZATION; NITROGEN; ANALOG; LENNOXAMINE; DISCOVERY;
D O I
10.1007/s00706-013-1146-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of 3-alkylideneisoindolinones was prepared by a Horner-Wadsworth-Emmons (HWE) reaction of aromatic aldehydes with N-(omega-hydroxyalkyl)substituted 3-phosphoisoindolin-1-ones, obtained in one-pot synthesis from 2-formylbenzoic acid. Additionally, the intramolecular HWE reaction of the N-(omega-formylalkyl)substituted phosphoisoindolin-1-ones afforded the corresponding isoindolone derivatives.
引用
收藏
页码:1001 / 1007
页数:7
相关论文
共 50 条
  • [41] Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactions
    Steinbach, Tobias
    Wahlen, Christian
    Wurm, Frederik R.
    POLYMER CHEMISTRY, 2015, 6 (07) : 1192 - 1202
  • [42] Reinvestigation of the Synthesis of Isoliquiritigenin: Application of Horner-Wadsworth-Emmons Reaction and Claisen-Schmidt Condensation
    Sano, Shigeki
    Okubo, Yoshinori
    Handa, Atsushi
    Nakao, Michiyasu
    Kitaike, Syuji
    Nagao, Yoshimitsu
    Kakegawa, Hisao
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (07) : 885 - 888
  • [43] ASYMMETRIC CARBOALKOXYALKYLIDENATION WITH A CHIRAL HORNER-WADSWORTH-EMMONS REAGENT
    DENMARK, SE
    RIVERA, I
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23): : 6887 - 6889
  • [44] Improved Horner-Wadsworth-Emmons olefination of aldehydes.
    Petroski, RJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U67 - U67
  • [45] A facile method for the stereoselective Horner-Wadsworth-Emmons reaction of aryl alkyl ketones
    Sano, S
    Yokoyama, K
    Shiro, M
    Nagao, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (05) : 706 - 709
  • [46] Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
    Moradei, OM
    duMortier, CM
    Cirelli, AF
    TETRAHEDRON, 1997, 53 (22) : 7397 - 7402
  • [47] Electronic effects on the Z(cis)-selectivity of Horner-Wadsworth-Emmons olefination reaction
    Reddy, AM
    Gopal, VR
    Rao, VJ
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (04): : 312 - 317
  • [48] INTRAMOLECULAR HORNER-WADSWORTH-EMMONS REACTION IN BASE SENSITIVE SUBSTRATES - ENANTIOSPECIFIC SYNTHESIS OF IRIDOID MONOTERPENE LACTONES
    NANGIA, A
    PRASUNA, G
    RAO, PB
    TETRAHEDRON LETTERS, 1994, 35 (22) : 3755 - 3758
  • [49] Aminooxylation Horner-Wadsworth-Emmons Sequence for the Synthesis of Enantioenriched γ-Functionalized Vinyl Sulfones
    Doherty, William
    Evans, Paul
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (04): : 1416 - 1424
  • [50] A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner-Wadsworth-Emmons reaction
    Krawczyk, Henryk
    Wasek, Katarzyna
    Kedzia, Jacek
    Wojciechowski, Jakub
    Wolf, Wojciech M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (02) : 308 - 318