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Synthesis and dynamic 1H NMR spectroscopic study of 1,4,6,7,8,9-hexahydro-3-methyl-1,4-diphenyl-7-thioxo-5H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5-one

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Abstract

3-Methyl-1-aryl-2-pyrazoline-5-one, aromatic aldehyde, and 6-amino-2-thiouracil were used for the synthesis of a variety of 1,4,6,7,8,9-hexahydro-3-methyl-1,4-diaryl-7-thioxo-5H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5-ones via a one-pot three-component reaction. The reaction was performed in the presence of piperidine as a catalyst that leads to reducing reaction time and improves synthetic efficiency. The free-energy barrier (ΔG ≠) for prototropic tautomerism in title compound is determined by dynamic 1H NMR studies to be 67 kJ mol−1.

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Authors and Affiliations

  1. Department of Chemistry, Imam Khomeini International University, Qazvin, Iran

    Mohammad Bayat, Shima Nasri & Mohammad Reza Mohammadali

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  1. Mohammad Bayat
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  2. Shima Nasri
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  3. Mohammad Reza Mohammadali
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Correspondence to Mohammad Bayat.

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Bayat, M., Nasri, S. & Mohammadali, M.R. Synthesis and dynamic 1H NMR spectroscopic study of 1,4,6,7,8,9-hexahydro-3-methyl-1,4-diphenyl-7-thioxo-5H-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5-one. Monatsh Chem 148, 1833–1842 (2017). https://doi.org/10.1007/s00706-017-2006-9

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  • DOI: https://doi.org/10.1007/s00706-017-2006-9

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