Abstract
AbstractChemical diversity is a strong driver in drug discovery, and chemical reactions that produce multi‐substituted heterocycles can result in significant chemical diversity. Here, we report a reaction that leads to highly substituted piperazinone derivatives in a single step. This was discovered accidently while reacting phenylglyoxal and anilines under Povarov conditions. We elucidated the structure of the compound formed when 2‐(4‐trifluoromethyphenyl)‐2‐oxoacetaldehyde was reacted with 4‐methoxyaniline as (1,4‐bis(4‐hydroxyphenyl)‐5‐[(4‐hydroxyphenyl)imino]‐3,6‐diphenylpiperazin‐2‐one) (5e). The structure was confirmed after extensive spectral analyses, including correlation spectroscopy, nuclear Overhauser effect spectroscopy, heteronuclear single quantum correlation spectroscopy, and heteronuclear multiple‐bond correlation nuclear magnetic resonance spectroscopy, in addition to high‐resolution mass spectrometry. This reaction is unprecedented and can potentially be exploited as a short route to highly diversified heterocycles.
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