Versatile approaches to a library of building blocks based on 5-acylthiazole skeleton

Abstract

Thiazole derivatives represent an important class of azole heterocycles with a broad spectrum of biological activity and, therefore, the synthesis of these compounds is of remarkable concern. We present here practical and reliable protocol for synthesis of some 5-acylthiazoles and demonstrate their utility in the preparation of several new series of thiazole-containing building blocks through transformation of 5-acyl function. Specifically, thiazole-based alcohols, oximes, primary, and secondary amines were successively synthesized in good to excellent yields. The chemical structures of obtained compounds were confirmed by ¹H and ¹³C NMR-spectroscopy, elemental analysis, and mass-spectrometry.

Graphical Abstract

Keywords:

• Building blocks
• Hantzsch thiazole synthesis
• Leuckart–Wallach reaction
• oxime
• thiazole

Acknowledgments

The authors thank V. I. Musatov, E. V. Vashchenko (STC “Institute for Single Crystals” NAS of Ukraine, Kharkiv, Ukraine), and A. V. Borisov (Enamine Ltd., Kiev, Ukraine) for spectroscopic measurements.

Additional information

Funding

The research was supported by [Grant 0118U002025] of Ministry of Education and Science of Ukraine and by [Grants 811H/11–09, 811H/38–09, 811H/26–10 and 811 H/19–12] of V.N. Karazin Kharkiv National University.