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
  • [21] Chemo-biocatalytic one-pot two-step conversion of cyclic amine to lactam using whole cell monoamine oxidase
    Zajkoska, Petra
    Cardenas-Fernandez, Max
    Lye, Gary J.
    Rosenberg, Michal
    Turner, Nicholas J.
    Rebros, Martin
    JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2017, 92 (07) : 1558 - 1565
  • [22] One-pot two-step chemoenzymatic deracemization of allylic alcohols using laccases and alcohol dehydrogenases
    Albarran-Velo, Jesus
    Gotor-Fernandez, Vicente
    Lavandera, Ivan
    MOLECULAR CATALYSIS, 2020, 493 (493)
  • [23] One-pot synthesis of heterocyclic beta-chlorovinyl aldehydes using Vilsmeier reagent
    Majo, VJ
    Perumal, PT
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19): : 6523 - 6525
  • [24] Two-Step One-Pot Synthesis of Pinoresinol from Eugenol in an Enzymatic Cascade
    Ricklefs, Esther
    Girhard, Marco
    Koschorreck, Katja
    Smit, Martha S.
    Urlacher, Vlada B.
    CHEMCATCHEM, 2015, 7 (12) : 1857 - 1864
  • [25] Polymerization of styrene and cyclization to macrocyclic polystyrene in a one-pot, two-step sequence
    Carnicom, Elizabeth M.
    Tillman, Eric S.
    REACTIVE & FUNCTIONAL POLYMERS, 2014, 80 : 9 - 14
  • [26] Straightforward Assembly of Phenylimidazoquinoxalines via a One-Pot Two-Step MCR Process
    De Moliner, Fabio
    Hulme, Christopher
    ORGANIC LETTERS, 2012, 14 (05) : 1354 - 1357
  • [27] One-pot two-step synthesis of N-arylcarbazole-based skeleton
    Tao, Sheng
    Liu, Ning
    Dai, Bin
    RSC ADVANCES, 2016, 6 (49): : 43250 - 43260
  • [28] Comparison of one-pot and two-step polymerization of polyimide from BPDA/ODA
    Inoue, H
    Sasaki, Y
    Ogawa, T
    JOURNAL OF APPLIED POLYMER SCIENCE, 1996, 60 (01) : 123 - 131
  • [29] An efficient one pot regioselective synthesis of a 3,3′-spiro-phosphonylpyrazole-oxindole framework via base mediated [1,3]-dipolar cycloaddition reaction of the Bestmann-Ohira reagent with methyleneindolinones
    Shelke, Anil M.
    Suryavanshi, Gurunath
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (32) : 8669 - 8675
  • [30] Convenient two-step one-pot synthesis of benzimidazoles using 2-nitroanilines and thiourea dioxide
    Pu, Shuai
    Liang, Qiuxiang
    Luo, Xi
    Luo, Juan
    JOURNAL OF CHEMICAL RESEARCH, 2014, (02) : 118 - 120