Synthesis, 1D and 2D NMR spectral assignments, and stereochemical studies of some 4,8,9,10-tetraaryl-1,3-diazaadamantan-6-one oximes
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A series of 4,8,9,10-tetraaryl-1,3-diazaadamantan-6-one oximes (4a-4e) have been synthesized. 1H and 13C NMR spectra of these oximes were recorded. Chemical shifts have been assigned and the stereochemistry of the compounds was established using 1D and 2D NMR spectral data. A detailed spectral investigation was carried out for one of the representative compounds (4a) with COSY, NOESY, HMQC, HMBC, DEPT-135, and N NMR spectral data. The NMR result clearly indicated the twin chair conformation of the two piperidine rings. The NMR results proved the axial orientation of two aryl groups (C4 and C10) in one piperidine ring and equatorial orientation of two aryl groups (C8 and C9) in another piperidine ring. The effect of allylic (A1,3) interaction between the oxime hydroxyl group and H-5e has been observed. Long-range coupling between H-10e and H-2 which are in ‘W’ arrangement is noted.
Keywords2D NMR 15N NMR Oxime Tricyclic compound Conformation W arrangement
The authors gratefully acknowledge DST- FIST NMR facility of Department of Chemistry, The Gandhigram Rural Institute-Deemed to be University for recording NMR spectra.
The authors thank the UGC, New Delhi, for Major Research Project (grant No. 42-358/2013 (SR)) and UGC-Special Assistance Programme (SAP).
Compliance with ethical standards
Conflict of interest
The authors declare that they have no conflict of interest.
- 6.Vijayakumar V, Sundaravadivelu M, Perumal S, Hewlins MJE (2000) NMR study of the stereochemistry of 2,4,6,8-tetraaryl-3,7-diazabicyclo [3.3.1] nonan-9-ones. Magn Reson Chem 38:883–885. https://doi.org/10.1002/1097-458X(200010)38:10<883::AID-MRC708>3.0.CO;2-V CrossRefGoogle Scholar
- 7.Vijayakumar V, Sundaravadivelu M, Perumal S (2001) NMR and IR spectroscopic study of mono-, bi- and tricyclic piperidone systems. Magn Reson Chem 39:101–104. https://doi.org/10.1002/1097-458X(200102)39:2<101::AID-MRC797>3.0.CO;2-F CrossRefGoogle Scholar
- 26.Ottaviani JI, Momma TY, Heiss C et al (2011) The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo. Free Radic Biol Med 50:237–244. https://doi.org/10.1016/j.freeradbiomed.2010.11.005 CrossRefGoogle Scholar