Highly regioselective synthesis of 2,4,5-(hetero) aryl substituted oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal alkynes

被引：74
|
作者：
Chatzopoulou, Elli [1 ]
Davies, Paul W. [1 ]
机构：
[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
来源：
CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 77期
关键词：
GOLD; CYCLOADDITION; NITRILES; 5-(3-INDOLYL)OXAZOLES; REARRANGEMENT; CATALYSIS; OXIDATION; MOIETIES; YLIDES; ACCESS;
D O I：
10.1039/c3cc45410j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A robust N-nucleophilic 1,3-N,O-dipole equivalent reacts with unsymmetrical internal alkynes under gold catalysis. Conjugation from a remote nitrogen lone pair enables and controls this convergent and highly regioselective process.
引用
收藏
页码：8617 / 8619
页数：3
相关论文
共 50 条
  • [1] Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition
    Davies, Paul W.
    Cremonesi, Alex
    Dumitrescu, Lidia
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) : 8931 - 8935
  • [2] Silver-Induced [3+2] Cycloaddition of Isocyanides with Acyl Chlorides: Regioselective Synthesis of 2,5-Disubstituted Oxazoles
    Liu, Jian-Quan
    Shen, Xuanyu
    Shatskiy, Andrey
    Zhou, Enlong
    Karkas, Markus D.
    Wang, Xiang-Shan
    CHEMCATCHEM, 2019, 11 (17) : 4272 - 4275
  • [3] Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition
    Raimondi, Wilfried
    Dauzonne, Daniel
    Constantieux, Thierry
    Bonne, Damien
    Rodriguez, Jean
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (31) : 6119 - 6123
  • [4] Efficient and Flexible Synthesis of Highly Functionalised 4-Aminooxazoles by a Gold-Catalysed Intermolecular Formal [3+2] Dipolar Cycloaddition
    Gillie, Andrew D.
    Reddy, Raju Jannapu
    Davies, Paul W.
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 226 - 239
  • [5] Direct [3+2]-cycloaddition of electron-deficient alkynes with CF3CHN2: Regioselective one-pot synthesis of 3-trifluoromethylpyrazoles
    Li, Feng
    Wang, Jingjing
    Pei, Wenlong
    Li, Hong
    Zhang, Huiling
    Song, Manman
    Guo, Linyun
    Zhang, Anan
    Liu, Lantao
    TETRAHEDRON LETTERS, 2017, 58 (46) : 4344 - 4347
  • [6] Cation radical [3+2] cycloaddition of chalcone epoxides:: A facile synthesis of highly substituted tetrahydrofurans
    Huo, CD
    Jia, XD
    Zhang, W
    Yang, L
    Lü, JM
    Liu, ZL
    SYNLETT, 2004, (02) : 251 - 254
  • [7] Synthesis of Trifluoromethyl-Substituted Ethyl Picolinate Derivatives by the Cobalt-Catalyzed Regioselective Intermolecular [2+2+2] Cycloaddition
    Ishikawa, Tomoki
    Sonehara, Taro
    Murakami, Shogo
    Minakawa, Maki
    Kawatsura, Motoi
    SYNLETT, 2016, 27 (13) : 2029 - 2033
  • [8] Regioselective Synthesis of Highly Functionalized Furans Through the RuII-Catalyzed [3+2] Cycloaddition of Diazodicarbonyl Compounds
    Xia, Likai
    Lee, Yong Rok
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (16) : 3430 - 3442
  • [9] Regioselective Synthesis of 2,4,5-Trisubstituted Oxazoles and Ketene Aminals via Hydroamidation and lodo-Imidation of Ynamides
    Mallick, Rajendra K.
    Prabagar, B.
    Sahoo, Akhila K.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19) : 10583 - 10594
  • [10] Stereoselective Synthesis of α-Diazo Oxime Ethers and Their Application in the Synthesis of Highly Substituted Pyrroles through a [3+2] Cycloaddition
    Lourdusamy, Emmanuvel
    Yao, Lin
    Park, Cheol-Min
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) : 7963 - 7967
12345