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
  • [1] BILOVIC D, 1967, CROAT CHEM ACTA, V39, P189
  • [2] Substituent Effects in Ugi-Smiles Reactions
    Cheron, Nicolas
    Ramozzi, Romain
    El Kaim, Laurent
    Grimaud, Laurence
    Fleurat-Lessard, Paul
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2013, 117 (33) : 8035 - 8042
  • [3] New Benzotriazole and Benzimidazole Scaffolds from Ugi-Smiles Couplings of Isocyanides
    Coffinier, Didier
    El Kaim, Laurent
    Grimaud, Laurence
    [J]. ORGANIC LETTERS, 2009, 11 (04) : 995 - 997
  • [4] Intramolecular cyclization reactions of 5-halo- and 5-nitro-substituted furans
    Crawford, KR
    Bur, SK
    Straub, CS
    Padwa, A
    [J]. ORGANIC LETTERS, 2003, 5 (18) : 3337 - 3340
  • [5] Lewis acid-catalyzed formation of Ugi four-component reaction product from Passerini three-component reaction system without an added amine
    Dai, Wei-Min
    Li, Huoming
    [J]. TETRAHEDRON, 2007, 63 (52) : 12866 - 12876
  • [6] Recent developments in isocyanide based multicomponent reactions in applied chemistry
    Dömling, A
    [J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89
  • [7] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
  • [8] 2-U
  • [9] Ugi post-condensation copper-triggered oxidative cascade towards pyrazoles
    Dos Santos, Aurelie
    El Kaim, Laurent
    Grimaud, Laurence
    Ronsseray, Caroline
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 1310 - 1314
  • [10] Phenol Ugi-smiles systems:: strategies for the multicomponent N-arylation of primary amines with isocyanides, aldehydes, and phenols
    El Kaïm, L
    Grimaud, L
    Oble, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) : 7961 - 7964