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Synthesis, characterization, X-ray diffraction studies and biological evaluation of tert-butyl 4-(2-ethoxy-2-oxoethyl)-piperazine-1-carboxylate and tert-butyl 4-(2-hydrazino-2-oxoethyl)piperazine-1-carboxylate

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Abstract

Two derivatives of N-Boc piperazine, an ester derivative, i.e., tert-butyl 4-(2-ethoxy-2-oxoethyl)-piperazine-1-carboxylate (1), and, a hydrazide derivative tert-butyl 4-(2-hydrazino-2-oxoethyl)piperazine-1-carboxylate (2) were synthesized and were characterized by FT-IR, 1H & 13C NMR and LCMS spectroscopic studies. The structures of both 1 and 2 were further confirmed by single crystal X-ray diffraction analysis. The molecule of 1 is linear in shape with the ethyl acetate moiety adopting fully extended conformation, while the molecule of 2 is L-shaped with the molecule being twisted at the C10 atom. The crystal structure of 1 adopts a two-dimensional zig-zag architecture featuring C–H…O intermolecular interactions, while that of 2 features strong N–H…O hydrogen bonds and intermolecular interactions of the type N–H…N and C–H…N, resulting in a two-dimensional structure. Furthermore, a detailed analysis of the intermolecular interactions and crystal packing of 1 and 2 via Hirshfeld surface analysis and fingerprint plots was performed. The antibacterial and antifungal activities of both the compounds have been studied against several microorganisms, and were found to be moderately active.

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Acknowledgments

The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysuru, for providing the single-crystal X-ray diffraction facility. The authors are also thankful to Sapala Organics Pvt. Ltd. Hyderabad, India for recording the FT-IR, 1H & 13C NMR and LCMS spectra. BK, TS, PH, and KM are thankful to the Management and to Dr. S. G. Gopala Krishna, Principal, Nagarjuna college of Engg. & Tech., Devanahalli, Bangalore, for providing laboratory facilities.

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Authors and Affiliations

  1. Department of Chemistry, Nagarjuna College of Engineering and Technology, Devanahalli, Bangalore, 562164, India

    Bhuvan Kulkarni & Manjunatha Kumsi

  2. Department of Physics, Nagarjuna College of Engineering and Technology, Devanahalli, Bangalore, 562164, India

    Sharada Thimmappaiah & Harisha Padigar

  3. Department of Chemistry, University College of Science, Tumkur University, Tumkur, 572103, India

    Suchetan Parameshwar Adimule

  4. Institution of Excellence, University of Mysore, VijnanaBhavan, Manasagangotri, Mysore, India

    Naveen Shivalingegowda

  5. Department of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India

    Lokanath Krishnappagowda Neratur

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  1. Bhuvan Kulkarni
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Correspondence to Manjunatha Kumsi.

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Kulkarni, B., Thimmappaiah, S., Padigar, H. et al. Synthesis, characterization, X-ray diffraction studies and biological evaluation of tert-butyl 4-(2-ethoxy-2-oxoethyl)-piperazine-1-carboxylate and tert-butyl 4-(2-hydrazino-2-oxoethyl)piperazine-1-carboxylate. Res Chem Intermed 42, 7375–7396 (2016). https://doi.org/10.1007/s11164-016-2542-7

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