One-Pot, Two-Step Conversion of Aldehydes to Phosphonyl- and Sulfonylpyrazoles Using Bestmann-Ohira Reagent

被引:63
|
作者
Kumar, Rahul [1 ]
Verma, Deepti [1 ]
Mobin, Shaikh M. [2 ]
Namboothiri, Irishi N. N. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
[2] Indian Inst Technol, Natl Single Crystal Xray Diffract Facil, Bombay 400076, Maharashtra, India
关键词
BASE-MEDIATED REACTION; REGIOSELECTIVE SYNTHESIS; DIAZOCARBONYL COMPOUNDS; PYRAZOLE; CYCLOADDITION; DERIVATIVES; CHEMISTRY; DIAZOALKANES; NITROALKENES; COMPLEXES;
D O I
10.1021/ol301695e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot, two-step, three-component method for the conversion of commercially available aldehydes to phosphonylpyrazoles has been developed, demonstrating, for the first time, the dual reactivity of the Bestmann-Ohira reagent (BOR) in a single-pot transformation. This method, extended to the synthesis of sulfonylpyrazoles by employing BOR in the first step and a diazomethyl sulfone in the second step, is complementary, with regard to regioselectivity, to the previous methods for the synthesis of such functionalized pyrazoles.
引用
收藏
页码:4070 / 4073
页数:4
相关论文
共 50 条
  • [1] The Bestmann-Ohira reagent for the conversion of aldehydes into terminal alkynes
    Zanatta, Shannon D.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2007, 60 (12) : 963 - 963
  • [2] One-pot conversion of activated alcohols into terminal alkynes using manganese dioxide in combination with the Bestmann-Ohira reagent
    Quesada, E
    Taylor, RJK
    TETRAHEDRON LETTERS, 2005, 46 (38) : 6473 - 6476
  • [3] Three-Component Domino Reaction Using the Bestmann-Ohira Reagent: A Regioselective Synthesis of Phosphonyl Pyrazole
    Zanda, Matteo
    SYNTHESIS-STUTTGART, 2010, (15): : A66 - A67
  • [4] Three-Component Reaction Using the Bestmann-Ohira Reagent: A Regioselective Synthesis of Phosphonyl Pyrazole Rings
    Mohanan, Kishor
    Martin, Anthony R.
    Toupet, Loic
    Smietana, Michael
    Vasseur, Jean-Jacques
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (18) : 3196 - 3199
  • [5] ORGN 364-One-pot regioselective synthesis of phosphonylpyrazoles via reaction of Bestmann-Ohira reagent with nitroalkenes
    Muruganantham, R.
    Mobin, Shaikh M.
    Namboothiri, Irishi N. N.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [6] A NEW ORGANOSILICON REAGENT FOR ONE-POT CONVERSION OF ALDEHYDES INTO TRIENALS
    BELLASSOUED, M
    REBOUL, E
    SALEMKOUR, M
    SYNTHETIC COMMUNICATIONS, 1995, 25 (20) : 3097 - 3108
  • [7] Two-Step One-Pot Reductive Amination of Furanic Aldehydes Using CuAlOx Catalyst in a Flow Reactor
    Nuzhdin, Alexey L.
    Bukhtiyarova, Marina V.
    Bukhtiyarov, Valerii I.
    MOLECULES, 2020, 25 (20):
  • [8] Preparation of nonsymmetrically substituted stilbenes in a one-pot two-step Heck strategy using ethene as a reagent
    Kormos, Chad M.
    Leadbeater, Nicholas E.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (10): : 3854 - 3858
  • [9] A straightforward one-pot two-step conversion of bile acids into dehomologated alcohols
    Hernandez-Huerta, Eduardo
    Flores-Alamo, Marcos
    Iglesias-Arteaga, Martin A.
    STEROIDS, 2021, 176
  • [10] A convenient two-step one-pot synthesis of phosphonamidates
    Mlodnosky, KL
    Holmes, HM
    Lam, VQ
    Berkman, CE
    TETRAHEDRON LETTERS, 1997, 38 (51) : 8803 - 8806