New one-pot, efficient, and regioselective method for the synthesis of 3-Trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs

TETRAHEDRON LETTERS

卷:53

Article

Bonacorso, Helio G.¹  Correa, Michele S.¹  Porte, Liliane M. F.¹  Pittaluga, Everton P.¹  Zanatta, Nilo¹  Martins, Marcos A. P.¹ 

[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil

关键词: Phenylpyrazoles;    3-Trifluoromethylpyrazoles;    Esterification reactions;    Cyclization reactions;    Phenylsemicarbazides;   

DOI  :  10.1016/j.tetlet.2012.07.119

来源: Elsevier

【 摘 要 】

An efficient and regioselective procedure for the synthesis of a series of alkyl(aryl/heteroaryl) substituted 3-trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs, from the cyclocondensation reactions of 4-alkoxy-1,1,1-trihaloalk-3-en-2-ones [CX3C(O)CR2=CR1(OMe/OEt), where R-1 = H, Me, Ph, 2-Furyl; R-2 = H; R-1-R-2 = -C4H8- and X = F, Cl] and 1-phenylsemicarbazide in an acidified alcoholic medium ((ROH)-O-3/H2SO4), where R-3 = Me, Et, Pr-i was successfully applied and is described here in detail. (C) 2012 Elsevier Ltd. All rights reserved.

【 授权许可】

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