Heterocyclic analogs of xanthiones: 5,6-fused 3-methyl-1-phenylpyrano[2,3-c]pyrazol-4(1H) thiones-synthesis and NMR ((1)H, (13)C, (15)N) data

Valerie Huemer; Gernot A Eller; Wolfgang Holzer

doi:10.1002/mrc.2609

Heterocyclic analogs of xanthiones: 5,6-fused 3-methyl-1-phenylpyrano[2,3-c]pyrazol-4(1H) thiones-synthesis and NMR ((1)H, (13)C, (15)N) data

Magn Reson Chem. 2010 Jun;48(6):476-82. doi: 10.1002/mrc.2609.

Authors

Valerie Huemer¹, Gernot A Eller, Wolfgang Holzer

Affiliation

¹ Department of Drug and Natural Product Synthesis, University of Vienna, A-1090 Vienna, Austria.

PMID: 20474027
DOI: 10.1002/mrc.2609

Abstract

Various [5,6]pyrano[2,3-c]pyrazol-4(1H)-thiones were synthesized in high yields by treatment of the corresponding [5,6]pyrano[2,3-c]pyrazol-4(1H)-ones with Lawesson's reagent. Detailed NMR spectroscopic studies were undertaken of the title compounds. Complete and unambiguous assignment of chemical shifts ((1)H, (13)C, (15)N) and coupling constants ((1)H,(1)H; (13)C,(1)H) was achieved by the combined application of various one- and two-dimensional (1D and 2D) NMR spectroscopic techniques. Unequivocal mapping of most (13)C,(1)H spin coupling constants is accomplished by 2D (delta, J) long-range INEPT spectra with selective excitation.

MeSH terms

Carbon Isotopes / chemistry
Heterocyclic Compounds / chemistry*
Magnetic Resonance Spectroscopy / methods*
Nitrogen Isotopes / chemistry
Protons
Thiones / chemical synthesis*

Substances

Carbon Isotopes
Heterocyclic Compounds
Nitrogen Isotopes
Protons
Thiones