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

Autor:	Wesley R. R. Harker, Joseph P. A. Harrity, Michael Simms, Matthew J. Tozer, Patrick M. Delaney
Rok vydání:	2013
Předmět:	2-Pyridone chemistry.chemical_compound chemistry Organic Chemistry Drug Discovery Structural isomer Regioselectivity Biochemistry Combinatorial chemistry Boronic acid Cycloaddition
Zdroj:	Tetrahedron. 69:1546-1552
ISSN:	0040-4020
DOI:	10.1016/j.tet.2012.12.010
Popis:	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-current chromatography allowing isolation of analytically pure 2-pyridones. Further derivatisations of trimethylsilyl-substituted 2-pyridone boronates were performed providing access to a selection of functionalised scaffolds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::96df787e55bba4cd84e87b5958951070 https://doi.org/10.1016/j.tet.2012.12.010 Zobrazit plný text záznamu Full Text from ScienceDirect