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

Kulkarni, Bhuvan and Sharada, T. and Padigar, H. and Adimule, S. P. and Gowda, N. S. and Krishnappagowda, L. and Lokanath, N. and Kumsi, M. (2016) 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. Research on Chemical Intermediates, 42 (10). pp. 7375-7396. ISSN 1568-5675

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Official URL: https://doi.org/10.1007/s11164-016-2542-7

Abstract

wo derivatives of N-Boc piperazine, an ester derivative, i.e., tert-butyl4-(2-ethoxy-2-oxoethyl)-piperazine-1-carboxylate (1), and, a hydrazide derivativetert-butyl 4-(2-hydrazino-2-oxoethyl)piperazine-1-carboxylate (2) were synthesizedand 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-raydiffraction analysis. The molecule of 1 is linear in shape with the ethyl acetate moietyadopting fully extended conformation, while the molecule of 2 is L-shaped with themolecule 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 inter-actions 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 crystalpacking of 1 and 2 via Hirshfeld surface analysis and fingerprint plots was performed.The antibacterial and antifungal activities of both the compounds have been studiedagainst several microorganisms, and were found to be moderately active.

Item Type: Article
Subjects: C Chemical Science > Chemistry
D Physical Science > Physics
Divisions: Department of > Institution of Excellence
Depositing User: manjula User
Date Deposited: 18 Jun 2019 10:55
Last Modified: 18 Jun 2019 10:55
URI: http://eprints.uni-mysore.ac.in/id/eprint/3368

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