On Reuben G. Jones synthesis of 2-hydroxypyrazines

Beilstein Journal of Organic Chemistry, Год журнала: 2022, Номер 18, С. 935 - 943

Опубликована: Июль 29, 2022

In 1949, Reuben G. Jones disclosed an original synthesis of 2-hydroxypyrazines involving a double condensation between 1,2-dicarbonyls and α-aminoamides upon treatment with sodium hydroxide at low temperature. This discovery turned out to be importance as even today there are no simple alternatives this preparation. Across the years, it was employed prepare but some its limits, notably regioselectivity issues when starting from α-ketoaldehydes, certainly hampered full-fledged generation pyrazine-containing new chemical entities potential interest in medicinal chemistry. The present text describes insights improvements, such unprecedented use tetraalkylammonium hydroxide, reaction parameters affecting yield phenylglyoxal two α-aminoamides. We also suggest mechanism explaining counterintuitive occurrence 3,5-substituted-2-hydroxypyrazine major product.

Язык: Английский

Notizen aus der Chemie

Nachrichten aus der Chemie, Год журнала: 2021, Номер 69(11), С. 56 - 59

Опубликована: Ноя. 1, 2021