An Efficient and Novel Regioselective Synthesis of Phosphonylpyrazoles from Vinylazides and Bestmann-Ohira Reagent

被引:10
|
作者
Madugula, Aravinda Kumar [1 ]
Mahendran, Vaithiyanathan [2 ]
Sridhara, Ajjanna Mahalingappa [3 ]
Rangaiah, Gururaja [1 ]
机构
[1] PRIST Univ, Ctr Res & Dev, Thanjavur 613403, Tamil Nadu, India
[2] Madurai Kamaraj Univ, Dept Organ Chem, Madurai 625021, Tamil Nadu, India
[3] Gomti Life Sci India Pvt Ltd, Bidadi Ind Area, Bangalore 562109, Karnataka, India
关键词
Phosphonylpyrazoles; Vinylazides; 1,3-dipolar cycloaddition; Regioselectivity; Bestmann-Ohira reagent;
D O I
10.13005/ojc/320524
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A novel and efficient reaction of vinyl azides with Bestmann-Ohira reagent for the regioselective synthesis of phosphonylpyrazoles is presented. Reaction proceeds through 1, 3 dipolar cycloaddition with an excellent yield in short period of time under mild reaction conditions. Moreover, no column purification is involved for the isolation of products.
引用
收藏
页码:2533 / 2541
页数:9
相关论文
共 50 条
  • [31] Efficient and Regioselective Synthesis of Novel Functionalized Dispiropyrrolidines and Their Cytotoxic Activities
    Yang, Jin-Ming
    Hu, Yu
    Li, Qiang
    Yu, Fan
    Cao, Jian
    Fang, Dong
    Huang, Zhi-Bin
    Shi, Da-Qing
    ACS COMBINATORIAL SCIENCE, 2014, 16 (03) : 139 - 145
  • [32] Efficient Synthesis of Structurally Novel Diaryl Ethers by Regioselective Functionalization
    Kharul, Rajendra K.
    Gite, Archana
    Goswami, Amitgiri
    Jain, Mukul
    Pandey, Bipin
    Patel, Pankaj R.
    SYNTHETIC COMMUNICATIONS, 2008, 38 (23) : 4282 - 4294
  • [33] Stannic chloride-iodine: An efficient reagent for regioselective synthesis of Furan-Fused heterocycles
    Majumdar, K. C.
    Biswas, A.
    Mukhopadhyay, P. P.
    SYNTHETIC COMMUNICATIONS, 2007, 37 (17) : 2881 - 2890
  • [34] Regioselective synthesis of chloro/bromostyrenes: Chloro/bromotrimethylsilane-nitrate salt as efficient reagent system
    Prakash, G. K. Surya
    Gurung, Laxman
    Mathew, Thomas
    Olah, George
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [35] Novel and efficient synthesis of pyrroloiminoquinones using a hypervalent iodine(III) reagent
    Kita, Y
    Watanabe, H
    Egi, M
    Saiki, T
    Fukuoka, Y
    Tohma, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (04): : 635 - 636
  • [36] Novel and efficient synthesis of pyrroloiminoquinones using a hypervalent iodine(III) reagent
    Jornal of the Chemical Society. Perkin Transactions 1, (04):
  • [37] Gadolinium(III) chloride: a novel and an efficient reagent for the synthesis of homoallylic alcohols
    Lingaiah, B. Venkat
    Ezikiel, G.
    Yakalah, T.
    Reddy, G. Venkat
    Rao, P. Shanthan
    TETRAHEDRON LETTERS, 2006, 47 (26) : 4315 - 4318
  • [38] Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction
    Delbrouck, Julien A.
    Tikad, Abdellatif
    Vincent, Stephane P.
    CHEMICAL COMMUNICATIONS, 2018, 54 (70) : 9845 - 9848
  • [39] Hexachloroethane: a highly efficient reagent for the synthesis of chlorosilanes from hydrosilanes
    Pongkittiphan, Veerachai
    Theodorakis, Emmanuel A.
    Chavasiri, Warinthorn
    TETRAHEDRON LETTERS, 2009, 50 (36) : 5080 - 5082
  • [40] A new reagent for the efficient synthesis of disulfides from alkyl halides
    Polshettiwar, V
    Nivsarkar, M
    Acharya, J
    Kaushik, MP
    TETRAHEDRON LETTERS, 2003, 44 (05) : 887 - 889