Rapid access to conformationally-constrained oxatricycles via Ugi-Smiles couplings

被引:9
作者
Richey, Bree [1 ]
Mason, Katelynn M. [1 ]
Meyers, Michael S. [1 ]
Luesse, Sarah B. [1 ]
机构
[1] So Illinois Univ, Dept Chem, Edwardsville, IL 62026 USA
关键词
Ugi-Smiles coupling; Diets-Alder cycloaddition; Oxatricycle; Epoxyisoindoline; Multicomponent coupling reaction; MULTICOMPONENT REACTIONS; ALDER CYCLOADDITION; PRODUCT; AMINES; REARRANGEMENT; HETEROCYCLES; FURANS; IMDAF;
D O I
10.1016/j.tetlet.2015.12.068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Use of allylamine and substituted 2-furaldehydes as components in Ugi-Smiles couplings of 2-nitrophenol provide ready access to N-aryl epoxyisoindolines. These adducts form via a dual event involving the Ugi-Smiles multicomponent reaction and an intramolecular Diets-Alder cycloaddition with the furan ring. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:492 / 494
页数:3
相关论文
共 37 条
  • [21] Complexity-enhancing acid-promoted rearrangement of tricyclic products of tandem Ugi 4CC/intramolecular Diels-Alder reaction
    Ilyin, Alexei
    Kysil, Volodymyr
    Krasavin, Mikhail
    Kurashvili, Irina
    Ivachtchenko, Alexandre V.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) : 9544 - 9547
  • [22] Recent applications of intramolecular Diels-Alder reactions to natural product synthesis
    Juhl, Martin
    Tanner, David
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) : 2983 - 2992
  • [23] Kappe CO, 1997, TETRAHEDRON, V53, P14179
  • [24] Keay BA, 1999, ADV CYCLOAD, V6, P173
  • [25] New substituted alkenyl-furfuryl-aryl amines: Synthesis and their characterization
    Mance, AD
    Jakopcic, K
    SindlerKulyk, M
    [J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (05) : 923 - 933
  • [26] New epoxyisoindolines by intramolecular Diels-Alder reactions of some methyl-substituted allylaryl-2-furfurylamines
    Mance, AD
    SindlerKulyk, M
    Jakopcic, K
    HergoldBrundic, A
    Nagl, A
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (04) : 1315 - 1322
  • [27] Cycloaddition-rearrangement sequence of 2-amido substituted furans as a method of synthesizing hexahydroindolinones
    Padwa, A
    Brodney, MA
    Satake, K
    Straub, CS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) : 4617 - 4626
  • [28] Intramolecular Diels-Alder Cycloaddition of Furans (IMDAF) for Natural Product Synthesis
    Padwa, Albert
    Flick, Andrew C.
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 110, 2013, 110 : 1 - 41
  • [29] Halo substituent effects on intramolecular cycloadditions involving furanyl amides
    Padwa, Albert
    Crawford, Kenneth R.
    Straub, Christopher S.
    Pieniazek, Susan N.
    Houk, K. N.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) : 5432 - 5439
  • [30] Preparation of tricyclic nitrogen heterocycles via tandem four-component condensation/intramolecular Diels-Alder reaction
    Paulvannan, K
    [J]. TETRAHEDRON LETTERS, 1999, 40 (10) : 1851 - 1854