Four-Component Synthesis of Polysubstituted Pyrazin-2(1H)-ones through a Ugi/Staudinger/Aza-Wittig/Isomerization Sequence

作者：Wu, Jing; Zhao, Long; Yang, Mao-Lin; Ding, Ming-Wu^*

来源：Journal of Organic Chemistry, 2021, 86(15): 10755-10761.

DOI：10.1021/acs.joc.1c00735

• SOLID-PHASE SYNTHESIS
• ONE-POT SYNTHESIS
• PYRAZINONES
• EFFICIENT
• 2(1H)-PYRAZINONES
• 2-PYRAZINONES
• 2-PYRIDONES
• ISOCYANIDES
• BMS-665053
• INHIBITORS

A new efficient synthesis of polysubstituted pyrazin-2(1H)-ones via the sequential Ugi/Staudinger/aza-Wittig/isomerization reaction has been developed. The four-component Ugi reactions of arylglyoxals 1, primary amines 2, a-azidovinyl acids 3, and isocyanides 4 produced the azides 5, which were treated with triphenylphosphine to give pyrazin-2(1H)-ones 6 in good yields through domino Staudinger/aza-Wittig/isomerization reactions.