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Synthesis, Spectroscopic Studies and X-ray Crystal Structures of New Pyrazoline and Pyrazole Derivatives

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Abstract

The synthesis and characterization of some pyrazoline compounds of 1,3-diketones with hydrazine derivatives, namely, 1-(S-benzyldithiocarbazate)-3-methyl-5-phenyl-5-hydroxypyrazoline (1); 1-(2-thiophenecarboxylic)-3-methyl-5-phenyl-5-hydroxypyrazoline (2); 1-(2-thiophenecarboxylic)-3,5-dimethyl-5-hydroxypyrazoline (3); 1-(S-benzyldithiocarbazato)-3-methyl-5-phenylpyrazole (4); 1-(2-thiophenecarboxylic)-3-methyl-5-phenylpyrazole (5) and 1-(S-benzyldithiocarbazate)-3,5-dimethylpyrazole (6) are reported. Studies by IR, (1H, 13C)-NMR spectroscopies and single crystal X-ray diffraction revealed that compounds (1), (2) and (3) are formed as pyrazoline, whereas (4) and (5) are formed as pyrazole derivatives only under acidic conditions. Compound (1) crystallizes in orthorhombic P212121, a = 6.38960(10) Å, b = 12.9176(3) Å, c = 21.2552(5) Å, (2) crystallizes in monoclinic, P21/n, a = 11.3617(2) Å, b = 8.4988(2) Å, c = 92.8900(10) Å and β = 92.8900(5)°, (3) crystallizes in monoclinic, C2/c, a = 15.9500(5) Å, b = 9.3766(3) Å, c = 16.6910(5) Å and β = 113.825(2)°, (4) crystallizes in monoclinic, P21/c, a = 15.228(4) Å, b = 5.5714(13) Å, c = 19.956(5) Å and β = 91.575(7)° and (6) crystallizes in orthorhombic, P212121, a = 5.3920(2) Å, b = 11.2074(5) Å, c = 21.885(1) Å. The (3) derivative represents the first pyrazoline compound prepared from 2,4-pentanedione and characterized crystallographically.

Graphical Abstract

The synthesis and characterization of some pyrazoline compounds of 1,3-diketones with hydrazine derivatives, namely, 1-(S-benzyldithiocarbazate)-3-methyl-5-phenyl-5-hydroxypyrazoline (1); 1-(2-thiophenecarboxylic)-3-methyl-5-phenyl-5-hydroxypyrazoline (2); 1-(2-thiophenecarboxylic)-3,5-dimethyl-5-hydroxypyrazoline (3); 1-(S-benzyldithiocarbazato)-3-methyl-5-phenylpyrazole (4); 1-(2-thiophenecarboxylic)-3-methyl-5-phenylpyrazole (5) and 1-(S-benzyldithiocarbazate)-3,5-dimethylpyrazole (6) are reported. Studies by IR, (1H, 13C)-NMR spectroscopies and single crystal X-ray diffraction revealed that compounds (1), (2) and (3) are formed as pyrazoline, whereas (4) and (5) are formed as pyrazole derivatives only under acidic conditions. Compound (1) crystallizes in orthorhombic P212121, a = 6.38960(10) Å, b = 12.9176(3) Å, c = 21.2552(5) Å, (2) crystallizes in monoclinic, P21/n, a = 11.3617(2) Å, b = 8.4988(2) Å, c = 92.8900(10) Å and β = 92.8900(5)°, (3) crystallizes in monoclinic, C2/c, a = 15.9500(5) Å, b = 9.3766(3) Å, c = 16.6910(5) Å and β = 113.825(2)°, (4) crystallizes in monoclinic, P21/c, a = 15.228(4) Å, b = 5.5714(13) Å, c = 19.956(5) Å and β = 91.575(7)° and (6) crystallizes in orthorhombic, P212121, a = 5.3920(2) Å, b = 11.2074(5) Å, c = 21.885(1) Å. The (3) derivative represents the first pyrazoline compound prepared from 2,4-pentanedione and characterized crystallographically.

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Acknowledgments

This work was sponsored by Grants from CNPq, FAPESP, FINEP (CT-INFRA 0970/01). GFS also gratefully acknowledges the financial support of the Conselho Nacional de Desenvolvimento Científico e Tecnológico-CNPq (Edital Universal-2007, Processo 307412/2008-3).

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Authors and Affiliations

  1. Instituto de Química, Universidade de Brasília, Brasília, DF, 70919-970, Brazil

    Gerimário F. de Sousa, Claudia C. Gatto & Inês S. Resck

  2. Instituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, 1350-250, Brazil

    Victor M. Deflon

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  1. Gerimário F. de Sousa
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  2. Claudia C. Gatto
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  4. Victor M. Deflon
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Correspondence to Gerimário F. de Sousa.

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de Sousa, G.F., Gatto, C.C., Resck, I.S. et al. Synthesis, Spectroscopic Studies and X-ray Crystal Structures of New Pyrazoline and Pyrazole Derivatives. J Chem Crystallogr 41, 401–408 (2011). https://doi.org/10.1007/s10870-010-9896-2

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  • DOI: https://doi.org/10.1007/s10870-010-9896-2

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