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Efficient synthesis of some new functionalized 3-amino- and 5-aminopyrazoles derivatives

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Abstract

Cyanoacetic acid hydrazide derivatives were utilized as key intermediates for the synthesis of some new 3-amino- and 5-aminopyrazole derivatives. Coupling of N′-phenylsulfonyl-2-cyanoacetohydrazide (1) and 1-(2-cyanoacetyl)-4-phenyl thiosemicarbazide (4) with different aryl diazonium chlorides afforded the corresponding 5-amino-1-substituted-4-pyrazolin-3-one derivatives 3 and 6, respectively. Treatment of ketene dithioacetal 9 and ketene-N,S-acetal 13 with hydrazine and/or benzenesulfonyl hydrazide furnished the corresponding 3-amino-5-1H-pyrazole-4-carbohydrazide derivatives 10, 11, and 14. The structures of the new synthesized compounds were elucidated and confirmed by elemental analyses and spectral data.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Mansoura University, Mansoura, 35516, Egypt

    Ehab Abdel-Latif & Abdel-Galil M. Khalil

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  1. Ehab Abdel-Latif
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  2. Abdel-Galil M. Khalil
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Correspondence to Ehab Abdel-Latif.

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Abdel-Latif, E., Khalil, AG.M. Efficient synthesis of some new functionalized 3-amino- and 5-aminopyrazoles derivatives. Res Chem Intermed 41, 4555–4567 (2015). https://doi.org/10.1007/s11164-014-1551-7

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  • DOI: https://doi.org/10.1007/s11164-014-1551-7

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