Cascade and multicomponent synthesis of structurally diverse 2-(pyrazol-3-yl)pyridines and polysubstituted pyrazoles

被引:5
作者
Barroso, Raquel [1 ,2 ]
Cabal, Maria-Paz [1 ,2 ]
Jimenez, Azucena [1 ,2 ]
Valdes, Carlos [1 ,2 ]
机构
[1] Univ Oviedo, Dept Quim Organ & Inorgan, C Julian Claveria 8, Oviedo 33004, Spain
[2] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, C Julian Claveria 8, Oviedo 33004, Spain
关键词
HALO-N-TOSYLHYDRAZONES; SIGMATROPIC REARRANGEMENT; COMPLEXES; DERIVATIVES; DISCOVERY; LIGANDS; INHIBITORS; INDOLES; DFT;
D O I
10.1039/c9ob02691f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cascade reaction between N-tosylhydrazones and 2-alkynylpyridines leads to 2-(pyrazol-3-yl)pyridines, important structural motifs in ligands for transition metals and bioactive molecules. When the reaction is conducted with 2,6-diethynylpyridine, the important 2,6-bis(pyrazolyl)pyridines are obtained, featuring the arrangement of tridentate and also pentadentate ligands. A novel three-component version of the reaction has been designed, which involves the use of alpha-bromo-N-tosylhydrazones, alkynylpyridines and NH-azoles. The generality of the multicomponent reaction is further illustrated by the preparation of different polysubstituted pyrazoles by employing an array of terminal alkynes. In these multicomponent reactions, complex molecules featuring three different heterocycles are assembled in a single step from commercial materials, enabling the fast generation of molecular diversity.
引用
收藏
页码:1629 / 1636
页数:8
相关论文
共 50 条
  • [1] Review: biologically active pyrazole derivatives
    Ansari, Anam
    Ali, Abad
    Asif, Mohd
    Shamsuzzaman
    [J]. NEW JOURNAL OF CHEMISTRY, 2017, 41 (01) : 16 - 41
  • [2] Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides
    Arendt, Kevin M.
    Doyle, Abigail G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) : 9876 - 9880
  • [3] Homo-and heteropolymetallic 3-(2-pyridyl)pyrazolate manganese and rhenium complexes
    Arroyo, Marta
    Gomez-Iglesias, Patricia
    Anton, Noelia
    Garcia-Rodriguez, Raul
    Alegria, Elisabete C. B. A.
    Pombeiro, Armando J. L.
    Miguel, Daniel
    Villafane, Fernando
    [J]. DALTON TRANSACTIONS, 2014, 43 (10) : 4009 - 4020
  • [4] Back to back 2,6-bis(pyrazol-1-yl)pyridine and 2,2′:6′,2"-terpyridine ligands: Untapped potential for spin crossover research and beyond
    Attwood, Max
    Turner, Scott S.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2017, 353 : 247 - 277
  • [5] Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines
    Barluenga, Jose
    Tomas-Gamasa, Maria
    Moriel, Patricia
    Amar, Fernando
    Valdes, Carlos
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) : 4792 - 4795
  • [6] Barluenga J, 2009, NAT CHEM, V1, P494, DOI [10.1038/nchem.328, 10.1038/NCHEM.328]
  • [7] Self-Assembly in Helical Columnar Mesophases and Luminescence of Chiral 1H-Pyrazoles
    Beltran, Eduardo
    Cavero, Emma
    Barbera, Joaquin
    Luis Serrano, Jose
    Elduque, Anabel
    Gimenez, Raquel
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (36) : 9017 - 9023
  • [8] Regioselective One-Step Synthesis of Pyrazoles from Alkynes and N-Tosylhydrazones: [3+2] Dipolar Cycloaddition/[1,5] Sigmatropic Rearrangement Cascade
    Carmen Perez-Aguilar, M.
    Valdes, Carlos
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) : 7219 - 7223
  • [9] Tetrahedral zinc complexes with liquid crystalline and luminescent properties:: Interplay between nonconventional molecular shapes and supramolecular mesomorphic order
    Cavero, Emma
    Uriel, Santiago
    Romero, Pilar
    Serrano, Jose Luis
    Gimenez, Raquel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (37) : 11608 - 11618
  • [10] 2-Phenyl and 2-heterocyclic-4-(3-(pyridin-2-yl)-1H-pyrazol-4-yl)pyridines as inhibitors of TGF-β1 and activin A signalling
    Ciayadi, Rudy
    Potdar, Mahesh
    Walton, Kelly L.
    Harrison, Craig A.
    Kelso, Geoffrey F.
    Harris, Simon J.
    Hearn, Milton T. W.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (18) : 5642 - 5645