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Molecules 2015, 20(5), 8223-8241; doi:10.3390/molecules20058223

Synthesis, Molecular Structure and Spectroscopic Investigations of Novel Fluorinated Spiro Heterocycles

1
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
2
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
3
Department of Chemistry, Rabigh College of Science and Art, King Abdulaziz University, P.O. Box 344, Rabigh 21911, Saudi Arabia
4
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
5
X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editors: Richard A. Bunce, Philippe Belmont, Wim Dehaen and Eugene Babaev
Received: 7 April 2015 / Revised: 29 April 2015 / Accepted: 29 April 2015 / Published: 7 May 2015
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

This paper describes an efficient and regioselective method for the synthesis of novel fluorinated spiro-heterocycles in excellent yield by cascade [5+1] double Michael addition reactions. The compounds 7,11-bis(4-fluorophenyl)-2,4-dimethyl- 2,4-diazaspiro[5.5] undecane-1,3,5,9-tetraone (3a) and 2,4-dimethyl-7,11-bis (4-(trifluoromethyl)phenyl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone (3b) were characterized by single-crystal X-ray diffraction, FT-IR and NMR techniques. The optimized geometrical parameters, infrared vibrational frequencies and NMR chemical shifts of the studied compounds have also been calculated using the density functional theory (DFT) method, using Becke-3-Lee-Yang-Parr functional and the 6-311G(d,p) basis set. There is good agreement between the experimentally determined structural parameters, vibrational frequencies and NMR chemical shifts of the studied compounds and those predicted theoretically. The calculated natural atomic charges using NBO method showed higher polarity of 3a compared to 3b.The calculated electronic spectra are also discussed based on the TD-DFT calculations. View Full-Text
Keywords: fluorine spiro-heterocycles; [5+1] cycloaddition; N,N-dimethylbarbituric acid; X-ray; DFT fluorine spiro-heterocycles; [5+1] cycloaddition; N,N-dimethylbarbituric acid; X-ray; DFT
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Islam, M.S.; Al-Majid, A.M.; Barakat, A.; Soliman, S.M.; Ghabbour, H.A.; Quah, C.K.; Fun, H.-K. Synthesis, Molecular Structure and Spectroscopic Investigations of Novel Fluorinated Spiro Heterocycles. Molecules 2015, 20, 8223-8241.

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