Synthesis and structure of (<i>R,S</i>)-2-methyl-4-(4-nitrophenyl)-pyrano[3,2-c]chromen-5(4<i>H</i>)-one

Authors

  • Rosica P. Nikolova Institute of Mineralogy and Crystallography, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Build. 107, 1113 Sofia
  • Boris Shivachev Institute of Mineralogy and Crystallography, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Build. 107, 1113 Sofia
  • Bozhana Mikhova Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Build. 9, 1113 Sofia
  • Bistra Stamboliyska Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Build. 9, 1113 Sofia
  • Kristina Mladenovska Department of Drug Design and Metabolism, Faculty of Pharmacy, Ss. Cyril and Methodious University, Skopje
  • Ana P. Panovska Department of Drug Design and Metabolism, Faculty of Pharmacy, Ss. Cyril and Methodious University, Skopje
  • Emil Popovski Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University, Skopje

DOI:

https://doi.org/10.20450/mjcce.2013.445

Keywords:

acenocoumarol, pyrano[3, 2-c]coumarin, crystal structure, DFT calcualations

Abstract

In this paper, the synthesis and structure of a novel pyrano[3,2-c]coumarin, which was obtained unexpectedly in a reaction of phosphoryl chloride and acenocoumarol, are presented. The chemical structure of the novel compound was elucidated by a detailed spectroscopic analysis based mainly on 1D and 2D NMR techniques. The structure was finally confirmed with a single-crystal X-ray analysis. The B3LYP/6-311+G** method correctly reproduces the bond lengths, bond angles, torsion angles, and other experimental spectroscopic data, which can be useful for investigating the characteristics of some structurally related molecules. Additionally, the title compound was obtained in high yields by performing a dehydratation reaction of acenocuomarol with acetic anhydride.  

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Published

2012-12-01

How to Cite

Nikolova, R. P., Shivachev, B., Mikhova, B., Stamboliyska, B., Mladenovska, K., Panovska, A. P., & Popovski, E. (2012). Synthesis and structure of (<i>R,S</i>)-2-methyl-4-(4-nitrophenyl)-pyrano[3,2-c]chromen-5(4<i>H</i>)-one. Macedonian Journal of Chemistry and Chemical Engineering, 32(2), 239–250. https://doi.org/10.20450/mjcce.2013.445

Issue

Vol. 32 No. 2 (2013)

Section

Organic Chemistry

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