Synthesis and properties of 6-alkynyl-5-aryluracils

Beilstein J Org Chem. 2024 Apr 22:20:898-911. doi: 10.3762/bjoc.20.80. eCollection 2024.

Abstract

The development of a new and straightforward chemoselective method for the synthesis of uracil-based structures by combining Suzuki-Miyaura and Sonogashira-Hagihara cross-coupling is reported. The methodology was applied to synthesize a series of novel compounds. The tolerance of the combination of different functional groups was tested. The influence of different functional groups on the physical properties was studied by ultraviolet-visible (UV-vis) and fluorescence spectroscopy, providing new insights into the potential applications of uracil-based structures.

Keywords: catalysis; cross-coupling; fluorescence; heterocycles; regioselectivity.

Grants and funding

We are grateful for the financial support of the State of Mecklenburg-Western Pomerania (Germany).