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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

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Abstract

This work describes the regioselective synthesis of two new series of 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-4,5-dihydro-5-hydroxy-5-(trihalomethyl)-1H-pyrazoles], where the 3-substituents are H, Me, C6H5, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-NO2C6H4, 4,4′-BiPh, and 2-furyl, in a one-pot methodology with ethanol as solvent, from the reaction of 4-alkoxy-4-(alkyl/aryl/heteroaryl)-1,1,1-trihaloalk-3-en-2-ones with oxalyldihydrazide (51–89%). Complementarily, the dehydration reactions of five examples of the described oxalylbispyrazolines are also reported, which furnished the respective 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-5-(trihalomethyl)-1H-pyrazoles] in 53–78% yields without the two C(O)–N bond cleavages.

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Acknowledgments

The authors acknowledge the financial support from Conselho Nacional de Desenvolvimento Científico e Tecnológico—CNPq (Proc. 303.296/2008-9). Fellowships from CAPES and CNPq are also acknowledged.

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Authors and Affiliations

  1. Núcleo de Química de Heterociclos, NUQUIMHE, Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil

    Helio G. Bonacorso, Cleber A. Cechinel, Jussara Navarini, Rosália Andrighetto, Marcos A. P. Martins & Nilo Zanatta

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  1. Helio G. Bonacorso
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  2. Cleber A. Cechinel
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  3. Jussara Navarini
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  4. Rosália Andrighetto
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  5. Marcos A. P. Martins
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  6. Nilo Zanatta
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Correspondence to Helio G. Bonacorso.

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Bonacorso, H.G., Cechinel, C.A., Navarini, J. et al. 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. Monatsh Chem 142, 277–285 (2011). https://doi.org/10.1007/s00706-011-0455-0

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