NMR spectral and structural studies on some xanthenones and their thiosemicarbazone derivatives: Crystal and molecular structure of 12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one

► BF 3:OEt 2 catalysed synthesis of tetrahydrobenzo[a]xanthen-11-ones. ► Synthesis of thiosemicarbazone derivatives and characterization by IR, 1D and 2D-NMR spectra. ► Single crystal XRD analysis of 12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one. A series of 12-aryl-8,9,10,12-tetrah...

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Bibliographic Details
Published in:Journal of molecular structure 2012-01, Vol.1008 (25), p.8-16
Main Authors: Sethukumar, A., Vithya, V., Udhaya Kumar, C., Arul Prakasam, B.
Format: Article
Language:English
Subjects:
2-naphthol
Catalysts
chemical structure
NMR
nuclear magnetic resonance spectroscopy
spectral analysis
Thiosemicarbazone
X-radiation
Xanthenone
XRD
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Summary:► BF 3:OEt 2 catalysed synthesis of tetrahydrobenzo[a]xanthen-11-ones. ► Synthesis of thiosemicarbazone derivatives and characterization by IR, 1D and 2D-NMR spectra. ► Single crystal XRD analysis of 12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one. A series of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones [ 1a– 9a] were prepared employing a three component one-pot reaction of aryl aldehyde, 2-naphthol and 1,3-cyclohexanedione using BF 3·OEt 2 as catalyst. Thiosemicarbazone derivatives [ 1b– 5b] were also prepared in the presence of acid catalyst. All the synthesized compounds have been characterized by IR and NMR. The structure of 5b was confirmed by HSQC spectral analysis. Single crystal X-ray structural analysis of 12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one evidences the envelope and flattened-boat conformations of cyclohexenone and pyran rings respectively.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2011.11.003