On Reuben G. Jones synthesis of 2-hydroxypyrazines

• Pierre Legrand and
• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

• occurrence of 3,5-substituted-2-hydroxypyrazine as the major reaction product. Keywords: α-aminoamide; condensation; hydroxypyrazine; methylglyoxal; phenylglyoxal; Introduction In a recent report [1], the many ways a pyrazine nucleus is able to interact with proteins were reviewed. In this text, it was

• amounts of such synthetic intermediates. As an illustration depicted in Scheme 4, the tetraethylammonium hydroxide-triggered condensation of either glyoxal (1{3}), methylglyoxal (1{4}), or the readily accessible [37] 2-(4-(benzyloxy)phenyl)-2-oxoacetaldehyde (1{5}) with phenylalanine amide hydrochloride

• (DMSO-d6) δ 158.9, 156.0, 139.5, 129.5, 128.6, 126.6, 126.3, 122.6, 39.1. Preparation of 3-benzyl-5-methylpyrazin-2-ol (3{4,2}). A 40% solution of methylglyoxal (1.94 g, 10.8 mmol) and phenylalanine amide hydrochloride (1.97 g, 9.8 mmol) were dispersed in methanol (26 mL). This was cooled to −78 °C