Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines

被引：36
作者：
Buev, Evgeny M. [1 ]
Moshkin, Vladimir S. [1 ]
Sosnovskikh, Vyacheslav Y. [1 ]
机构：
[1] Ural Fed Univ, Inst Nat Sci, Dept Chem, Ekaterinburg 620000, Russia
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 08期
基金：
俄罗斯科学基金会;
关键词：
FLASH VACUUM THERMOLYSIS; ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; STEREOSPECIFIC SYNTHESIS; 3-SUBSTITUTED COUMARINS; DECARBOXYLATIVE ROUTE; 2-AZAALLYL ANIONS; N-OXIDE; DERIVATIVES; 5-ARYLOXAZOLIDINES;
D O I：
10.1021/acs.orglett.6b00475
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nonstabilized azomethine ylides are easily trapped by anthraquinone to form stable spiro-oxazolidines, which have an unusual ability to undergo a cycloreversion in the presence of other dipolarophiles at 120-150 degrees C. All tested recycloadditions with carbonyl compounds and electron-poor alkenes occurred in moderate to high yields (41-92%). Moreover, increasing the reaction temperature to 210 degrees C made it possible to obtain adducts with low reactive dipolarophiles.
引用
收藏
页码：1764 / 1767
页数：4
相关论文
共 49 条
  • [1] ACHIWA K, 1985, CHEM PHARM BULL, V33, P1975
  • [2] Facile Dearomatization of Nitroquinolines through [3+2] and [4+2] Cycloaddition Reactions
    Bastrakov, Maxim A.
    Starosotnikov, Alexey M.
    Kachala, Vadim V.
    Fedyanin, Ivan V.
    Shevelev, Svyatoslav A.
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (02) : 146 - 153
  • [3] TRIMETHYLAMINE N-OXIDE AS A PRECURSOR OF AZOMETHINE YLIDES
    BEUGELMANS, R
    NEGRON, G
    ROUSSI, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (01) : 31 - 32
  • [4] DEPROTONATION OF N-OXIDES OF ALIPHATIC-AMINES - GENERAL REACTIONAL SCHEME AND NEW PYRROLIDINE SYNTHESIS
    BEUGELMANS, R
    BENADJILAIGUERTSIRA, L
    CHASTANET, J
    NEGRON, G
    ROUSSI, G
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (03): : 725 - 734
  • [5] Chemoselective 1,3-dipolar cycloadditions of azomethine ylide with conjugated dienes
    Blumberg, Laura C.
    Costa, Brian
    Goldstein, Rebecca
    [J]. TETRAHEDRON LETTERS, 2011, 52 (08) : 872 - 874
  • [6] Synthesis of (alkylaminomethyl)lactones and hydroxypiperidones using alkylaminomethylation methodology
    Buev, Evgeny M.
    Moshkin, Vladimir S.
    Sosnovskikh, Vyacheslav Y.
    [J]. TETRAHEDRON LETTERS, 2015, 56 (47) : 6590 - 6592
  • [7] Castulik J., 2001, TETRAHEDRON, V57, P8339
  • [8] CHASTANET J, 1985, HETEROCYCLES, V23, P653
  • [9] Intramolecular dipolar cycloaddition reactions of azomethine ylides
    Coldham, I
    Hufton, R
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2765 - 2809
  • [10] 1,3-Dipolar Cycloaddition-Decarboxylation Reactions of an Azomethine Ylide with Isatoic Anhydrides: Formation of Novel Benzodiazepinones
    D'Souza, Asha M.
    Spiccia, Nadia
    Basutto, Jose
    Jokisz, Pawel
    Wong, Leon S. -M.
    Meyer, Adam G.
    Holmes, Andrew B.
    White, Jonathan M.
    Ryan, John H.
    [J]. ORGANIC LETTERS, 2011, 13 (03) : 486 - 489
12345