Synthesis and characterization of some new 1,2,3-thiadiazole and 1,2,3-selenadiazole triterpene derivatives from allobetulone and 2-oxoallobetulin

Abstract

The synthesis of new 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives from triterpenoid ketones has been investigated via the corresponding semicarbazones. The intermediates 5, 8 have also been isolated, separated and their structures identified. The Hurd–Mori reaction and Lalezari method have been applied to synthesize a series of new substances 6 and 7. The regioselectivity of the functionalization mostly was centered at the C-3 position for the products 9 and 10. The structures of these compounds were confirmed by 2D-NMR spectroscopy.

Graphical Abstract

Keywords:

• Triterpenoid ketone
• semicarbazone
• Hurd–Mori reaction
• Lalezari method

Acknowledgments

The author would like to thank Prof. Wim Dehaen for his valuable discussions and guidance, the Technical Assistants at University of Leuven, Belgium for valuable advice and help.

Disclosure statement

No potential conflict of interest was reported by the authors.