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
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