An improved microwave-assisted facile one-pot synthesis of novel pyrazolylphosphonates via Knoevenagel-phospha-Michael protocol

被引:0
|
作者
Mahdjoub, Sara [1 ]
Derabli, Chamseddine [1 ]
Yildirim, Muhammet [2 ]
Boulcina, Raouf [3 ,4 ]
Debache, Abdelmadjid [3 ]
机构
[1] Natl Higher Sch Biotechnol Toufik Khaznadar, Dept Biotechnol, Constantine, Algeria
[2] Bolu Abant Izzet Baysal Univ, Fac Sci & Arts, Dept Chem, Bolu, Turkiye
[3] Mentouri Constantine 1 Univ, Lab Synth Mol Biol Interest, Constantine 25000, Algeria
[4] Batna 2 Univ, Fac Technol, Dept Engn Proc, Batna, Algeria
关键词
BESTMANN-OHIRA REAGENT; DERIVATIVES; ANTIOXIDANT; PYRAZOLE;
D O I
10.1002/jhet.4825
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, a highly effective microwave-assisted method employing a multicomponent domino Knoevenagel/phospha-Michael reaction has been established. This approach facilitates the synthesis of a novel set of pyrazolylphosphonate derivatives in good yields by combining aryl aldehydes with pyrazolones and trialkylphosphites, utilizing piperidine as a Bronsted base catalyst. All pyrazolylphosphonates have been characterized by means of IR, 1H-NMR, 13C-NMR, and HRMS analyses and physical methods. This protocol can be characterized by its eco-friendly nature, exceptional efficiency in terms of product yields, and short reaction times. This study describes a microwave-assisted method employing a domino Knoevenagel/phospha-Michael reaction, enabling the synthesis of pyrazolylphosphonate derivatives from aryl aldehydes, pyrazolones, and trialkylphosphites with piperidine as a catalyst. image
引用
收藏
页码:1045 / 1056
页数:12
相关论文
共 50 条
  • [1] Microwave-assisted synthesis of fused piperazine-benzimidazoles via a facile, one-pot procedure
    Song, Gui-Ting
    Li, Shi-Qiang
    Yang, Zhi-Wei
    Yuan, Jian-Hui
    Wang, Ming-Shu
    Zhu, Jin
    Chen, Zhong-Zhu
    Xu, Zhi-Gang
    TETRAHEDRON LETTERS, 2015, 56 (31) : 4616 - 4618
  • [2] Aqueous microwave-assisted DMAP catalyzed synthesis of β-phosphonomalonates and 2-amino-4H-chromen-4-ylphosphonates via a domino Knoevenagel-phospha-Michael reaction
    Kour, Parteek
    Kumar, Anil
    Rai, Vijai K.
    COMPTES RENDUS CHIMIE, 2017, 20 (02) : 140 - 145
  • [3] Microwave-assisted novel one-pot synthesis and characterization of copper oxide
    Bhatta, Lakshminarayana Kudinalli Gopalakrishna
    Gundanna, Susheel Kumar
    Venkatesh, Krishna
    Bhatta, Umananda Manjunatha
    CHEMICAL PAPERS, 2021, 75 (06) : 2597 - 2601
  • [4] Microwave-assisted novel one-pot synthesis and characterization of copper oxide
    Lakshminarayana Kudinalli Gopalakrishna Bhatta
    Susheel Kumar Gundanna
    Krishna Venkatesh
    Umananda Manjunatha Bhatta
    Chemical Papers, 2021, 75 : 2597 - 2601
  • [5] Efficient Microwave-assisted One-pot Synthesis of Novel Spironaphthopyrano-one Derivatives
    Meshram, G.
    Wagh, P.
    Amratlal, V.
    Deshpande, S.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) : 1639 - 1645
  • [6] A microwave-assisted facile one-pot synthesis of annelated pyridines from β-formyl enamides via Henry reaction
    Chetia, A
    Longchar, M
    Lekhok, KC
    Boruah, RC
    SYNLETT, 2004, (07) : 1309 - 1311
  • [7] Mesoporous titania-ceria mixed oxide (MTCMO): a highly efficient and reusable heterogeneous nanocatalyst for one-pot synthesis of β-phosphonomalonates via a cascade Knoevenagel-phospha-Michael addition reaction
    Mohammed, Mohammed Salim
    Bakhtiarian, Mohsen
    Bahrami, Kiumars
    JOURNAL OF EXPERIMENTAL NANOSCIENCE, 2020, 15 (01) : 54 - 69
  • [8] A Simple and Green Tandem Knoevenagel-Phospha-Michael Reaction for One-Pot Synthesis of 2-Oxindol-3-ylphosphonates Catalyzed by a DABCO-Based Ionic Liquid
    Song, Lan-Lan
    Yang, Cheng
    Yu, Ya-Qin
    Xu, Da-Zhen
    SYNTHESIS-STUTTGART, 2017, 49 (07): : 1641 - 1647
  • [9] One-pot and microwave-assisted synthesis of N-sulfonylaziridines
    Xu, Hao
    Tian, Hua
    Zheng, Liangyu
    Liu, Qingwen
    Wang, Li
    Zhang, Suoqin
    TETRAHEDRON LETTERS, 2011, 52 (22) : 2873 - 2875
  • [10] Microwave-assisted one-pot synthesis of novel fluorinated octahydroquinazolinone derivatives as antibacterial agents
    Okoro, Cosmas
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250