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Eco-friendly synthesis and antioxidant activity of new trifluoromethyl-substituted N-(pyrimidin-2-yl)benzo[d]thiazol-2-amines and some N-derivatives

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Abstract

A convenient and environmentally benign procedure for the synthesis of a new series of trifluoromethyl-substituted N-(pyrimidin-2-yl)benzo[d]thiazol-2-amines by the cyclocondensation reaction of (benzo[d]thiazolyl)guanidine with either 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones or 2,2,2-trifluoro-1-(2-methoxycyclohexen-1-en-1-yl)ethanone is described. The main reactions were performed in refluxing water as the solvent (8–24 h), without catalysts, and the corresponding new N-(pyrimidinyl)-1H-(benzo[d]thiazolyl)amines were obtained at a 60–88 % yield. Subsequently, some di(hetero)arylamines were derivatized to the respective tertiary amines via easy N-alkylation and N-alkenylation reactions at 55–82 % yields. Finally, the Lipinski parameters and the total antioxidant activity of the new series of secondary arylamines were also evaluated.

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Acknowledgments

The authors thank the Coordination for Improvement of Higher Education Personnel (CAPES) for the fellowships, as well as the National Council for Scientific and Technological Development (CNPq) for financial support (Process numbers 306.883/2015-5 and 471.269/2013-1-CNPq/Universal).

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Authors and Affiliations

  1. Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97.105-900, Brazil

    Helio G. Bonacorso, Tainara P. Calheiro, Melissa B. Rodrigues, Nilo Zanatta & Marcos A. P. Martins

  2. Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, Santa Maria, RS, 97.105-900, Brazil

    Sílvio T. Stefanello & Félix A. A. Soares

Authors
  1. Helio G. Bonacorso
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  2. Tainara P. Calheiro
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  3. Melissa B. Rodrigues
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  4. Sílvio T. Stefanello
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  5. Félix A. A. Soares
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  6. Nilo Zanatta
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  7. Marcos A. P. Martins
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Corresponding author

Correspondence to Helio G. Bonacorso.

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Bonacorso, H.G., Calheiro, T.P., Rodrigues, M.B. et al. Eco-friendly synthesis and antioxidant activity of new trifluoromethyl-substituted N-(pyrimidin-2-yl)benzo[d]thiazol-2-amines and some N-derivatives. Monatsh Chem 147, 2185–2194 (2016). https://doi.org/10.1007/s00706-016-1829-0

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  • DOI: https://doi.org/10.1007/s00706-016-1829-0

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