Novel Multicomponent Domino Approach to 2,5-Bifunctionalized Five-Membered Cyclic Nitrones

被引：5
|
作者：
Buchlovic, Marian [1 ]
Man, Stanislav [1 ]
Potacek, Milan [1 ]
机构：
[1] Masaryk Univ, Dept Chem, CS-61137 Brno, Czech Republic
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 06期
关键词：
allenes; alcohols; aldehydes; domino reactions; multicomponent reactions; nitrones; 1,3-DIPOLAR CYCLOADDITION; TANDEM REACTIONS; BUILDING-BLOCKS; TRANSFORMATIONS; UNDERSTAND; RADICALS; STRATEGY; PROTEIN;
D O I：
10.1055/s-0031-1289726
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Multicomponent reactions of 2,2-dimethylpenta- 3,4-dienal oxime with aldehydes and primary alcohols were studied and the optimum conditions for preparing a new family of 2,5-substituted five-membered cyclic nitrones were identified. This reaction offers direct access to the target structures in a single synthetic step. The scope and limitations of the reaction were evaluated, and all products were isolated and fully characterized.
引用
收藏
页码：973 / 982
页数：10
相关论文
共 50 条
  • [21] Stereochemical Determination of Five-Membered Cyclic Ether Acetogenins Using a Spin-Spin Coupling Constant Approach and DFT Calculations
    Gutierrez-Cepeda, Adrian
    Hernandez Daranas, Antonio
    Fernandez, Jose J.
    Norte, Manuel
    Souto, Maria L.
    MARINE DRUGS, 2014, 12 (07): : 4031 - 4044
  • [22] Recent Advances in the Synthesis of Five-Membered Cyclic Carbonates and Carbamates from Allylic or Propargylic Substrates and CO2
    Vranjesevic, Filip
    Kolympadi Markovic, Maria
    Matulja, Dario
    Ambrozic, Gabriela
    Angel Sordo, Jose
    Laclef, Sylvain
    Vrcek, Valerije
    Markovic, Dean
    CATALYSTS, 2022, 12 (05)
  • [23] Synthesis of Five-Membered Cyclic Guanidines via Cascade [3+2] Cycloaddition of α-Haloamides with Organo-cyanamides
    Wang, Chuan-Chuan
    Qu, Ya-Li
    Liu, Xue-Hua
    Ma, Zhi-Wei
    Yang, Bo
    Liu, Zhi-Jing
    Chen, Xiao-Pei
    Chen, Ya-Jing
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (04): : 3546 - 3554
  • [24] "Give me five" - an amino imidazoline-2-imine ligand stabilises the first neutral five-membered cyclic triel(i) carbenoides
    Denker, Lars
    Trzaskowski, Bartosz
    Frank, Rene
    CHEMICAL COMMUNICATIONS, 2021, 57 (22) : 2816 - 2819
  • [25] Divergent Synthesis of Novel Five-Membered Heterocyclic Compounds by Base-Mediated Rearrangement of Acrylamides Derived from a Novel Isocyanide-Based Multicomponent Reaction
    Basso, Andrea
    Banfi, Luca
    Riva, Renata
    MOLECULES, 2011, 16 (10): : 8775 - 8787
  • [26] Kinetic Study and NBO Analysis of the Dehydrogenation Mechanism of Five-membered Ring Heterocyclic 2,5-Dihydro-[furan, thiophene, selenophene
    Shiroudi, Abolfazl
    Zahedi, Ehsan
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (11) : 2249 - 2256
  • [27] A flexible route towards five-membered ring imino sugars and their novel 2-deoxy-2-fluoro analogues
    Ayad, T
    Génisson, Y
    Broussy, S
    Baltas, M
    Gorrichon, L
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) : 2903 - 2910
  • [28] Preparation and properties of novel thermotropic liquid crystalline hyperbranched polyesters composed of five-membered heterocyclic mesogen by A2+B3 approach
    Sato, Moriyuki
    Matsuoka, Yoichi
    Yamaguchi, Isao
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2007, 45 (14) : 2998 - 3008
  • [29] A novel construction of living polymerization by neighboring group participation: Living cationic ring-opening polymerization of a five-membered cyclic dithiocarbonate
    Choi, W
    Sanda, F
    Endo, T
    MACROMOLECULES, 1998, 31 (25) : 9093 - 9095
  • [30] Direct synthesis of N2-unprotected five-membered cyclic guanidines by regioselective [3+2] annulation of aziridines and cyanamides
    Wang, Chuan-Chuan
    Wang, Xin-Lu
    Zhang, Qing-Ling
    Liu, Juntao
    Ma, Zhi-Wei
    Liu, Zhi-Jing
    Chen, Ya-Jing
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (06): : 1574 - 1579
12345