Efficient and highly regioselective synthesis of ethyl 1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylates under ultrasound irradiation

被引：33
|
作者：
Machado, Pablo [1 ]
Lima, Glauber R. [1 ]
Rotta, Mariane [1 ]
Bonacorso, Helio G. [1 ]
Zanatta, Nilo [1 ]
Martins, Marcos A. P. [1 ]
机构：
[1] Univ Fed Santa Maria, Nucl Quim Heterociclos NUQUIMHE, Dept Quim, Ctr Ciencias Nat & Exatas, BR-97105900 Santa Maria, RS, Brazil
来源：
ULTRASONICS SONOCHEMISTRY | 2011年 / 18卷 / 01期
关键词：
Ultrasound; Pyrazoles; Enones; X-ray; Rimonabant analogues; HALOACETYLATED ENOL ETHERS; PYRAZOLE DERIVATIVES; BIOLOGICAL EVALUATION; RECEPTOR ANTAGONISTS; PROMOTED SYNTHESIS; LIGANDS; KETONES; DESIGN; POTENT; O-17;
D O I：
10.1016/j.ultsonch.2010.06.009
中图分类号：
O42 [声学];
学科分类号：
070206 ; 082403 ;
摘要：
A series of 14 ethyl 1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylates has been synthesized from the cyclocondensation reaction of ethyl 4-methoxy-2-oxoalk[cycloalk]-3-enoates [EtO2CC(O)C(R-2) = C(R-I)OR, where R = H, Me: R-I = Pr, Ph, 4-MeOC6H4, 4-MeC6H4, 4-FC6H4, 4-CIC6H4, 4-BrC6H4, 4-NO2C6H4, fur-2-yl; R-2 = R-1, R-2 = -(CH2)(3)-. -(CH2)(4)-, -(CH2)(5)-, -(CH2)(6)-, 3,4-dihydronaphth-2-yll with 2,4-dichlorophenyl hydrazine hydrochloride under ultrasound irradiation with high regioselectivity and in 71-92% yields. The main goal of this methodology was the significant reduction of reaction times. The compounds were obtained after irradiation for 10-12 min. In addition, the structure of the ethyl 1H-pyrazole-3-carboxylates was supported by crystallographic data. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码：293 / 299
页数：7
相关论文
共 50 条
  • [21] Design, synthesis, antimicrobial activity, and mechanism of novel 3-(2,4-dichlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives
    Zheng, Yuguo
    Chen, Mei
    Zhang, Renfeng
    Xue, Wei
    PEST MANAGEMENT SCIENCE, 2024, 80 (10) : 5388 - 5399
  • [22] Crystal structure of (2E)-2-[1-(4-bromophenyl)-3-(1H-imidazol-1-yl) propylidene]-N-(2,4-dichlorophenyl) hydrazinecarboxamide, C19H16BrCl2N5O
    Al-Wabli, Reem I.
    Attia, Mohamed I.
    Ghabbour, Hazem A.
    El-Sayed, Nahed N. E.
    Fun, Hoong-Kun
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2015, 230 (03): : 217 - 218
  • [23] Regioselective Synthesis of 5-and 3-Hydroxy-N-Aryl-1H-Pyrazole-4-Carboxylates and Their Evaluation as Inhibitors of Plasmodium falciparum Dihydroorotate Dehydrogenase
    Vah, Luka
    Medved, Tadej
    Groselj, Uros
    Klemencic, Marina
    Podlipnik, Crtomir
    Stefane, Bogdan
    Wagger, Jernej
    Novinec, Marko
    Svete, Jurij
    MOLECULES, 2022, 27 (15):
  • [24] Synthesis, Crystal Structure and Antitumor Activity of 3-(2,4-dichlorophenyl)-2-phenyl-5-(p-tolyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine
    Liu, Jin
    Zhao, Juan
    Lu, Jiu-fu
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2020, 42 (04): : 591 - 596
  • [25] Facile, diversity-orientated one-pot synthesis of ethyl 1,5-disubstituted-1H-1,2,4-triazole-3-carboxylates
    Degorce, Sebastien
    Delouvrie, Benedicte
    Davey, Paul R. J.
    Didelot, Myriam
    Germain, Herve
    Harris, Craig S.
    Lambert-van der Brempt, Christine
    Lebraud, Honorine
    Ouvry, Gilles
    TETRAHEDRON LETTERS, 2012, 53 (45) : 6078 - 6082
  • [26] Switchable highly regioselective synthesis of 3,4-dihydro-quinoxalin-2(1H) ones from o-phenylenediamines and aroylpyruvates
    Dobias, Juraj
    Ondrus, Marek
    Addova, Gabriela
    Bohac, Andrej
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 1350 - 1360
  • [27] Computational study: Synthesis, spectroscopic (UV-vis, IR, NMR), antibacterial, antifungal, antioxidant, molecular docking and ADME of new (E)-5-(1-(2-(4-(2,4-dichlorophenyl)thiazol-2-yl)hydrazineylidene) ethyl)-2,4-dimethylthiazole
    Gangurde, Keshav B.
    Adole, Vishnu A.
    Ghotekar, Dattatray S.
    RESULTS IN CHEMISTRY, 2023, 6
  • [28] Triethanolamine as an inexpensive and efficient catalyst for the green synthesis of novel 1H-pyrazolo[1,2-a]pyridazine-5,8-diones under ultrasound irradiation in water and their antibacterial activity
    Khoraamabadi-zad, Ahmad
    Azadmanesh, Mohammad
    Karamian, Roya
    Asadbegy, Mostafa
    Akbari, Maryam
    RSC ADVANCES, 2014, 4 (88): : 47721 - 47725
  • [29] A Convenient and Efficient Protocol for the One Pot Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones Catalyzed by Ionic Liquids under Ultrasound Irradiation
    Dadhania, Abhishek N.
    Patel, Vaibhav K.
    Raval, Dipak K.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2011, 22 (03) : 511 - 516
  • [30] Crystal structure of ethyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17FN2O2
    Tong, Sheng-Yue
    You, Jin-Zong
    Zhang, Yi-Ping
    Wang, Zhen-Zhen
    Yu, Ke-Ji
    Hu, Qiong
    Pan, Hui-Juan
    Wu, Cheng-Jie
    Qi, De-Qiang
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2018, 233 (02): : 269 - 270
12345