Tetrahedron

Scalable synthesis of functionalised 2-pyridones via [4+ 2] cycloaddition reactions of 2-pyrazinones and alkynylboronates

WRR Harker, PM Delaney, M Simms, MJ Tozer…

Index: Harker, Wesley R.R.; Delaney, Patrick M.; Simms, Michael; Tozer, Matthew J.; Harrity, Joseph P.A. Tetrahedron, 2013 , vol. 69, # 5 p. 1546 - 1552

Full Text: HTML

Citation Number: 2

Abstract

The multigram synthesis of N-protected 2-pyridone boronic acid derivatives via a [4+ 2] cycloaddition of alkynylboronates with 2-pyrazinones is presented. The reactions are highly chemoselective, and generally highly regioselective although trimethylsilyl-substituted alkynylboronates have proven to be an exception. Nonetheless, in this latter case, separation of regioisomers was successfully accomplished via high performance counter- ...