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Crystal Structure of Ethyl 6-Amino-5-cyano-4-(4-fluorophenyl)- 2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate

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Abstract

Ethyl 6-amino-5-cyano-4-(4-fluorophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate was synthesized based on a commercially available trisodium citrate dihydrate as an inexpensive and eco-friendly catalyst for the first-time via one-pot tandem Knoevenagel-cyclocondensation of malononitrile, 4-f luorobenzaldehyde and in situ generated ethyl 5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate in aqueous ethanol at room temperature and its crystal structure is determined by X-ray structure analysis. The crystals are triclinic, sp. gr. \(P\bar 1\), a = 8.7914(7) Å, b = 11.3632(8) Å, c = 11.4005(9) Å, α = 62.278(7)°, β = 71.099(7)°, γ = 80.856(6)°, Z = 2, R = 0.0544 for 2491 observed ref lections. Pyran and pyrazole rings are almost coplanar and phenyl ring is almost perpendicular to these two rings. Pyran ring adopts boat conformation. The crystal structure is stabilized by N–H···N, N–H···O, C–H···F, and C–H···π hydrogen interactions. In addition, a number of weak π···π interactions also contribute to stabilize the crystal structure.

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Authors and Affiliations

  1. X-ray Crystallography Laboratory, Post-Graduate Department of Physics and Electronics, University of Jammu, Jammu, India

    Balbir Kumar & Vivek K. Gupta

  2. Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Visva-Bharati (a Central University), Santiniketan, West Bengal, India

    Bubun Banerjee & Goutam Brahmachari

Authors
  1. Balbir Kumar
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  2. Bubun Banerjee
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  3. Goutam Brahmachari
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  4. Vivek K. Gupta
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Correspondence to Vivek K. Gupta.

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Kumar, B., Banerjee, B., Brahmachari, G. et al. Crystal Structure of Ethyl 6-Amino-5-cyano-4-(4-fluorophenyl)- 2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate. Crystallogr. Rep. 63, 388–393 (2018). https://doi.org/10.1134/S1063774518030057

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  • DOI: https://doi.org/10.1134/S1063774518030057

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