115584-11-7Relevant articles and documents
Facile synthesis of N-benzylated 3-alkyl-2,6-diarylpiperidin-4-ones: Stereochemical investigation by 1D/2D NMR and single-crystal XRD
Dindulkar, Someshwar D.,Parthiban, Paramasivam,Puranik, Vedavati G.,Jeong, Yeon Tae
, p. 44 - 56 (2011)
A series of thirteen 1-benzyl-3-alkyl-2,6-diarylpiperidin-4-ones 14-26 were conveniently synthesized in high yields 87-92%. In order to find the impact on piperidone stereochemistry, beside the N-benzylation, methyl/ethyl/isopropyl groups at C-3 and halo/
Synthesis and NMR spectral studies of some 2,6-diarylpiperidin-4-one O-benzyloximes
Parthiban,Balasubramanian,Aridoss,Kabilan
, p. 11 - 24 (2008)
Variously substituted 2,6-diarylpiperidin-4-one O-benzyloximes were synthesized by the direct condensation of the corresponding 2,6-diarylpiperidin-4-ones with O-benzylhydroxylamine hydrochloride. All the synthesized compounds are characterized by IR, Mass and NMR spectral studies. NMR spectral assignments are made unambiguously by their one-dimensional (1H NMR and 13C NMR) and two-dimensional (1H-1H COSY, NOESY, HSQC and HMBC) NMR spectra. All the synthesized compounds are resulted as single isomer, i.e., exclusively E isomer (9-14). The conformational preference of 2,6-diarylpiperidin-4-one oxime ethers with and without alkyl substituents at C-3 and C-5 has also been discussed using the spectral studies. The observed chemical shifts and coupling constants suggest that compounds 8-13 adopt normal chair conformation with equatorial orientation of all the substituents while compound 14 contributes significant boat conformation along with the predominant chair conformation in solution. The effect of oximination on ring carbons, their associated protons, alkyl substituents and ipso carbons are studied. Every proton in the piperidone ring of the oxime ether is observed as distinct signal due to oximination. The order of chemical shift magnitude in compound 8 is H-2a > H-6a > H-5e > H-3e > H-3a > H-5a. For 9-12, the order is H-6a > H-5e > H-2a > H-3a > H-5a, for 13, H-6a > H-2a > H-5e > H-3a > H-5a and for 14, the order is H-2a > H-6a > H-5e > H-3a > H-5a while the 13C chemical shift magnitude for 8-14 due to oximination is C-2 > C-6 > C-3 > C-5.
Stereoselective synthesis, spectral and antimicrobial studies of some cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones
Velayutham Pillai,Rajeswari,Vidhyasagar
, p. 174 - 182 (2014)
A series of novel cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones were synthesized stereoselectively and characterized by IR, Mass, 1H NMR, 13C NMR, 1H-1H COSY and 1H-13C COSY spectra. The stereochemistry of the synthesized compounds was established using NMR spectra. Antimicrobial screening of the synthesized compounds revealed their antibacterial and antifungal potencies. Growth inhibition of Enterobacter Aerogenes by compound 15 was found to be superior to the standard drug.
Synthesis, NMR spectral studies and antimicrobial evaluation of some 2-(benzothiazol-2-yl)-1-(alkyl-2r,6c-diarylpiperidin-4-ylidine)hydrazine derivatives
Xavier, J. John Francis,Venkateswaramoorthi,Kamaraj,Krishnasamy
, p. 5105 - 5111 (2013)
Substituted 2-(benzothiazol-2-yl)-1-(alkyl-2,6-diarylpiperidin-4-ylidine) hydrazines 10-17 were synthesized by the condensation of different 2r,6c-diarylpiperidin-4-ones 1-8 with 2-hydrazinobenzothiazole 9. All the synthesized compounds were investigated in solution and in the solid state by IR, 1H, 13C and 2D NMR spectral techniques. The structure-activity relationships were studied by the screening of the antimicrobial activity over a representative panel of bacterial and fungal strains using two-fold serial dilution method.
Design, synthesis, spectral and biological evaluation of novel 1-allyl substituted 2,6-diphenylpiperidin-4-ones and its derivatives of oximes/oxime ethers
Narayanan, Kuppusamy,Shanmugam, Mani,Jothivel, Sarangan,Kabilan, Senthamaraikannan
, p. 6602 - 6607,6 (2012)
A series of 1-allyl-2,6-diphenylpiperidin-4-one oximes 17-24 and 1-allyl-2,6-diphenylpiperidin-4-one O-benzyloximes 25-32 were synthesized from respective 1-allyl-2,6-diphenylpiperidin-4-ones 9-16. The structure and the conformations have been investigated for all the synthesized compounds 9-32 by analytical and spectral techniques (IR, Mass, 1H, 13C, 2D NMR and X-ray Diffraction). Based on the proton NMR analysis, all the synthesized compounds 9-32, exposed chair conformation except compounds 22 and 30 (twist boat conformation). For all the synthesized compounds 9-32 antimicrobial activity has been carried out against a panel of selected bacterial and fungal strains using Streptomycin and Amphotericin B as standards. Antibacterial and antifungal activity of compounds 19, 21, 23 (allyl oximes) 25-29, 31, 32 (allyl oxime ethers) and 11, 13 (ketones) exerted moderate to excellent activity against Staphylococcus aureus, Bacillus subtilis, Salmonella typhi bacterial strains and Penicillium chrysogenum, Aspergillus niger, Fusarium oxysporum fungal strains. The MIC results of all the synthesized compounds revealed that most of the oxime ether compounds exhibit excellent activity against selected bacterial and fungal strains.
Synthesis, spectral characterization, solution and solid-state conformations of N-nitroso-2,7-diaryl-1,4-diazepan-5-ones by NMR and XRD studies
Ponnuswamy, M. N.,Ponnuswamy, S.,Sethuvasan, S.,Sugumar, P.
, (2020/08/10)
Nitroso derivative of 2,7-diaryl-1,4-diazepan-5-ones 9–12 are synthesized and characterized using spectroscopic techniques such as IR, EI-MS and NMR spectra. The stereochemical investigation of nitroso compounds has been carried out with 1D (1H, 13C & DEPT-135) and 2D (COSY & HSQC) NMR spectral data. Rotational isomers (syn and anti rotamers) of 9–12 are identified and categorized by room temperature NMR spectral studies. Furthermore, the conformation of the ring and the orientation of N–N=O function have been arrived on the basis of chemical shifts, coupling constants and dihedral angles. In solution state, syn and anti rotamers of the compounds 9–11 exist in equilibrium between flattened boat conformation with quasi-axial orientations of the aryl groups at C-2 and C-7. Nevertheless, compound 12 and its syn and anti rotamers prefer to adopt equilibrium between chair conformations with axial orientation of aryl substituents. In order to validate the solution state conformation, the compound 12 is crystallized and the crystal structure is solved by single crystal XRD study. The compound 12 exists in an alternate chair conformation and aryl groups at C-2 & C-7 occupy axial orientations in solid state also.
Cross-linked polystyrene/titanium tetrachloride as a tightly bound complex catalyzed the modified Mannich reaction for the synthesis of piperidin-4-ones
Rahmatpour, Ali,Emen, Reza,Amini, Ghazal
, p. 24 - 33 (2019/05/10)
Cross-linked polystyrene beads were prepared, characterized and the resulting polymer carrier was functionalized with titanium tetrachloride (TiCl4)via complexation of polystyrene with TiCl4 to afford the corresponding cross-linked polystyrene-TiCl4 stable complex (PSt/TiCl4)in an one step reaction and characterized by FT-IR, UV, TGA, DSC, XRD, SEM, BET. This tightly bound coordination complex was used as a water tolerant, heterogeneous, recoverable and reusable Lewis acid catalyst for the synthesis of substituted piperidin-4-ones via the modified Mannich multi-component condensation of ketones, aromatic aldehydes, and ammonium acetate in 1:2:1 M ratio under mild conditions. The rate of reactions was found to decrease with an increasing percentage of crosslinking and the mesh size of the copolymer beads. The catalyst is water tolerant, stable and can be easily recovered and reused at least four times without any loss of activity.
New thiazoldinone substituted 2,6-diarypiperidin-4-one: Synthesis, crystal structure, spectral characterization, binding mode with calf thymus DNA
Sangeetha,Sankar,Tharini
, (2019/08/20)
A series of 2,6-diarylpiperidin-4-ylidene thiazolidin-4-one derivatives (15–21) were efficiently synthesized using a green and recyclable catalyst Amberlit IR-120H resin under microwave irradiation. All the compounds were characterized by elemental analys
Synthesis, stereochemical and biological studies of some N-cyclohexylcarbamoyl -2,6-diarylpiperidin-4-ones
Sethukumar,Anand, P. Surendar,Kumar, C. Udhaya,Prakasam, B. Arul
, p. 352 - 362 (2016/11/04)
A series of N-cyclohexylcarbamoylpiperidin-4-ones were synthesized by the addition reaction of corresponding piperidin-4-ones with cyclohexylisocyanate in benzene. The structure and stereochemistry of the synthesized N-cyclohexylcarbamoyl -2, 6-diarylpiperidin-4-ones, were established on the basis of their analytical and spectral data (IR, 1H and 13C NMR). 2D NMR spectra (HOMOCOSY, HSQC, HMBC and NOESY) were also recorded to analyze the stereochemistry. In the IR spectra of synthesized compounds, the characteristic absorptions due to ring and amide carbonyl functionalities were observed which evidences the formation of N-cyclohexylcarbamoyl-2, 6-diarylpiperidin-4-ones. NMR spectral results are in line with the proposed structure of the compounds synthesized. Conformational analysis was carried out from the extracted coupling constants and NOESY spectral results. The synthesized compounds were evaluated for their antibacterial and antifungal activities.
Stereoselective synthesis and spectral studies of some benzotriazolylacetyl hydrazones of 3–alkyl–2,6–diarylpiperidin–4–ones
Pillai, M. Velayutham,Rajeswari,Kumar, C. Udhaya,Krishnan, K. Gokula,Mahendran,Ramalingan,Nagarajan,Vidhyasagar
, p. 558 - 565 (2017/09/19)
An effort to include biologically potent benzotriazole nucleus into piperidine ring is achieved through hydrazone formation. The characterization of the synthesized compounds was carried out using FT-IR, 1H &13C NMR, 1H–1H COSY, 1H–13C COSY, NOESY spectral techniques and GC-Mass spectrum. The spectral assignments were done without ambiguity using 2D-NMR techniques. The conformational preference of the piperidine ring deduced from the spectral studies is ‘chair’. The diastereotopic nature of the methylene protons/methyl groups present in the molecules is revealed clearly in their spectral pattern observed.
