Synthesis of 3-methoxy-quinoxalin-2-ones from methyl trimethoxyacetate and phenylenediamines

An Aniline-Mediated Regioselective Synthesis of Quinoxalin-2-ones via the Condensation of α-Ketimine Esters with 2-Aminoanilines

“…This steric phenomenon has also previously been reported for the condensation of 2-aminoanilines with methyl trimethoxyacetate. 20 The scope of the chemistry was extended to study possible substituent effects of the α-keto ester starting material ( Table 2). Additional screening of α-keto esters found that…”

Ytterbium Triflate Catalyzed Synthesis of Heterocycles

“…Venable et al coupled methyl trimethoxyacetate with o-phenylenediamines using a catalytic amount of Yb(OTf) 3 to yield 3methoxyquinoxalin-2-ones in moderate to good yields. 150 The reaction proceeded regioselectively, resulting in only the single isomer when 3-substituted 1,2-phenylenediamines were subjected to the reaction conditions. Recently, Kumar and co-workers also reported an acid-catalyzed microwave-assisted synthesis of 2-phenylimidazo[1,2-a]pyridylquinoxalin-2(1H)-ones via Hinsberg heterocyclization between 2-phenylimidazo[1,2-a]pyridine-3-glyoxalates and o-phenylenediamine.…”