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Ukr. Bioorg. Acta 2021, Vol. 16, N2, 23-28.

Synthesis and NMR spectroscopy investigations of functionalized spiropyranochromenediones and their spirothiadiazole derivatives

Viktoria S. Moskvina1,2*, Olexander V. Turov1, Tetyana V. Shokol1, Volodymyr P. Khilya1

1 Taras Shevchenko National University of Kyiv, Volodymyrska St., 64, Kyiv
2 V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine,
1 Murmanska St., Kyiv, 02094, Ukraine

tel.: +380-44-239-3342; e-mail: v.moskvina@gmail.com

ABSTRACT
This investigation focuses on the synthesis of spiropyranoneoflavones and the modification of obtained compounds at the exocyclic oxygen atom. Kabbe cyclization of 6-acetyl-7-hydroxy-8-methyl-4-phenyl-2H-chromene-2-one with cyclohexanone or cyclopentanone in the presence of pyrrolidine provided 10-methyl-4-phenyl-2H-spiro[cyclohexane(cyclopentane)-1,8-pyrano[3,2-g]chromene]-2,6(7H)-diones. Their new functionalized derivatives with thiosemicarbazide residues were synthesized. Acetylation of obtained thiosemicarbazones with acetic anhydride proceeded via cyclization of thiosemicarbazide fragment into 1,3,4-thiadiazole ring to give corresponding N-[3'-acetyl-10-methyl-8-oxo-6-phenyl-3'H,8H-dispiro[cyclohexane-1,2-pyrano[3,2-g]chromene-4,2'-[1,3,4]thiadiazol]-5'-yl]acetamide and N-[3'-acetyl-10-methyl-8-oxo-6-phenyl-3'H,8H-dispiro[cyclopentane-1,2-pyrano[3,2-g]chromene-4,2'-[1,3,4]thiadiazol]-5'-yl]acetamide. The structure of the obtained compounds was confirmed by NMR spectroscopy.

KEYWORDS
spiro compounds; neoflavones; spiropyranochromenediones; NMR spectroscopy; heteronuclear correlation.

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