Novel Asymmetric Thiazolyl-Substituted Penta-1,4-Dien-3-Ones and 3,5-Diaryl-2-Pyrazolines

Abstract

Various diaryl/hetaryl representatives of penta-1,4-dien-3-one series attract the attention of synthetic chemists during several decades owing to the possibility of their consequent chemical modification resulted in obtaining compounds of potential interest to materials science. In addition to their synthetic importance, title diarylideneacetones can be applied directly as medical drugs, such as antioxidants and anti-inflammatory agents. In this communication, we report the synthesis of a series of new asymmetric thiazole cycle containing diarylideneacetones, which further demonstrated high regioselectivity in their reaction with hydrazine. To clarify this feature, quantum-chemical modeling of the cyclization process was conducted.

Keywords:

• Diarylideneacetones
• penta-14-dien-3-ones
• 1H-pyrazolines
• regioselectivity
• spin-spin coupling

Acknowledgements

The authors express their gratitude to Enamine Ltd., Kyiv, Ukraine for providing chemicals, measuring all the necessary spectra and for any other kinds of support. This work was performed using computational facilities of a joint computer cluster of SSI “Institute for Single Crystals” and Institute for Scintillation Materials of National Academy of Science of Ukraine incorporated into Ukrainian National Grid.

Additional information

Funding

This work was supported in part by the Research Grants of the Ministry of Education and Science of Ukraine 0118U002025 and 0119U002536.