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
  • [41] An efficient and regioselective synthesis of 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-5-(trihalomethyl)-1H-pyrazoles] from 4-alkoxy-1,1,1-trihaloalk-3-en-2-ones
    Bonacorso, Helio G.
    Cechinel, Cleber A.
    Navarini, Jussara
    Andrighetto, Rosalia
    Martins, Marcos A. P.
    Zanatta, Nilo
    MONATSHEFTE FUR CHEMIE, 2011, 142 (03): : 277 - 285
  • [42] Synthesis and Crystal Structure of 1-(3-(2-Fluoro-6-chlorophenyl)-5-methylisoxazole-4-carbonyl)-3-phenyl-4-benzoyl-1H-pyrazole
    Guo, You-Yuan
    Wang, Huan
    Ma, Xin
    Zhang, Shuai-Qi
    Fu, Ying
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 30 (01) : 5 - 9
  • [43] An Efficient Synthesis of New 5-(1-Aryl-1H-pyrazole-4-yl)-1H-tetrazoles from 1-Aryl-1H-pyrazole-4-carbonitriles via [3+2] Cycloaddition Reaction
    dos Santos, Mauricio S.
    Bernardino, Alice M. R.
    Pinheiro, Luiz C. S.
    Canto-Cavalheiro, Marilene M.
    Leon, Leonor L.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (06) : 1425 - 1428
  • [44] FACILE AND EFFICIENT REGIOSELECTIVE SYNTHESIS OF 1-(3′-SUBSTITUTED QUINOXALIN-2′-YL)-3-ARYL/HETEROARYL-5-METHYLPYRAZOLES
    Aggarwal, Ranjana
    Masan, Eakta
    Sumran, Garima
    SYNTHETIC COMMUNICATIONS, 2013, 43 (13) : 1842 - 1848
  • [45] Synthesis of 2,4-dihydrochromeno[3,4-d][1,2,3]triazoles and 5-(2H-chromen-3-yl)-1H-tetrazoles via regioselective 1,3-dipolar cycloaddition of 2H-chromene-3-carbonitriles with NaN3
    Mishra, Deepak R.
    Panda, Bhabani S.
    Ahemad, Mohammed A.
    Nayak, Sabita
    Mohapatra, Seetaram
    CHEMISTRYSELECT, 2022, 7 (46):
  • [46] A facile and regioselective synthesis of some new pyrimido[4,5-d] [1,2,4]triazolo[1,5-a]pyrimidinediones catalyzed by Zn(BDC)-MOF under ultrasound irradiation
    Abdollahi-Basir, Mohammad Hossein
    Shirini, Farhad
    Tajik, Hassan
    Ghasemzadeh, Mohammad Ali
    JOURNAL OF MOLECULAR STRUCTURE, 2019, 1195 : 302 - 308
  • [47] Stereoselective synthesis of 2-substituted 6-[1-(2,6-difluorophenyl)ethyl]-5-methylpyrimidin-4(3H)-ones
    Mai, A.
    Artico, M.
    Rotili, D.
    Novakov, I. A.
    Orlinson, B. S.
    Navrotskii, M. B.
    Eremiichuk, A. S.
    Gordeeva, E. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (10) : 1531 - 1534
  • [48] Synthesis, Crystal Structure, Antitumor Activities and Docking Study of 1-(2-(1H-Indol-3-yl)ethyl)-3-(2-methoxyphenyl)urea
    Hu Chun-Hong
    Wei Dui-Dui
    Sun Xiao-Fei
    Lin Rui-Li
    Hu Min-Min
    Tang Lei
    Wang Zhen
    He Dian
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2018, 37 (03) : 393 - 399
  • [49] Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives
    Liu, Xing-Hai
    Zhao, Wen
    Shen, Zhong-Hua
    Xing, Jia-Hua
    Yuan, Jing
    Yang, Guo
    Xu, Tian-Ming
    Peng, Wei-Li
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (15) : 3626 - 3628
  • [50] Synthesis, spectroscopic investigation and computational study of 3-(1-(((methoxycarbonyl)oxy)imino)ethyl)-2H-chromen-2-one
    Krishnan, K. Gokula
    Sivakumar, R.
    Thanikachalam, V.
    Saleem, H.
    Doss, M. Arockia
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 144 : 29 - 42
12345