new spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cycloaddition reaction and their conformational structures

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ID: 179553
2014
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Abstract
Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone and 2,4-diaryl-1'H-spiro[bicyclo[3.3.1]nonane-3,5'-pyrimidine]-2',4',6',9(3'H)-tetraone, respectively in good yield. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR, UV-Visible, mass spectroscopy and X-ray crystallography techniques. A possible mechanism of the formation is discussed. The structural conformation also demonstrated by coupling constants derived from dihedral angles between vicinal and geminal protons. The 1H NMR spectra of NH protons of spiro compounds derived from barbituric acid show a broad singlet peak instead, these protons in the spiro compounds derived from thiobarbituric acid show two distinct peaks. DOI: http://dx.doi.org/10.4314/bcse.v28i3.12
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pesyan2014bulletinnew Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors ;N. N. Pesyan;S. Noori;S. Poorhassan;E. Şahin
Journal Experimental physiology
Year 2014
DOI
http://dx.doi.org/10.4314/bcse.v28i3.12
URL
http://www.ajol.info/index.php/bcse/article/view/108087
Keywords
conformation michael addition spiro barbituratechemistry

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