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

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.