One-pot synthesis of a new class of alkynyl anionic synthons: the 4-(2',2-trimethylsilylethynylphenoxymethyl)-2H-chromen-2-ones

Abstract

An efficient approach for the synthesis of a new class of anionic synthons: the 4-(2',2-trimethylsilylethynylphenoxymethyl)-2H-chromen-2-ones employing a one-pot three-component reaction is reported. Reaction of trimethylsilylacetylene, o-iodophenol and nine different bromomethylcoumarins in THF solvent at 80 °C under sealed tube conditions gave nine novel 4-(2',2-trimethylsilylethynylphenoxymethyl)-2H-chromen-2-ones in greater than 90% isolated yields. All compounds were spectroscopically characterized by elemental analysis, FT-IR, MS, ¹H-, and ¹³C-NMR techniques.

Graphical Abstract

Keywords:

• Alkynyl anionic synthons
• one-pot reactions
• cross-coupling reactions
• palladium/copper-catalyzed reactions

Acknowledgments

Grateful thanks to: (1) Bangalore University, Jnana Bharathi Campus, Bengaluru - 560056; (2) Bengaluru City University, Central College Campus, Palace Road, Bengaluru – 560001 for providing relevant necessary bench-work facilities; (3) Vision Group on Science and Technology, Government of Karnataka, INDIA, Grant No. VGST/CESEM/2018-19/GRD-745/2019-20/362/1 dated 10th January 2020; and (4) Jawaharlal Nehru Centre for Advanced Scientific Research, Bangalore; and Prof. H. Ila for RA to JCAS.