The triple bond of nitrile is stable and usually needs strong nucleophiles (LiAlH<sub>4</sub> or Grignard reagents) or strong acids/bases under refluxing for nucleophilic addition reactions. Also, transition-metal catalysts are required for nitrile to proceed coupling reactions with other functional groups. By utilizing anodic oxidation, a coupling reaction of imine (C=N) with nitrile (C≡N) to form quinazoline ring was obtained without transition-metal catalysts or harsh reaction conditions. Quinazoline ring is a key structure in various pharmaceutical targets such as antibacterial, antiviral, anticonvulsant, and anticancer drugs. We developed a green pathway of quinazoline synthesis via electrochemical pathway. Since harmful transitional-metal catalysts and hazardous chemical reagents are not utilized, their corresponding toxic chemical wastes are excluded. This electrochemical reaction offers an environment-friendly and clean pathway to synthesize quinazoline derivatives. Also, it is the first nitrile coupling reaction using electrochemical way. Detail information will be discussed in the meeting.

Anodic coupling of imine with nitrile: Transition-metal-free synthesis of quinazoline derivatives

253rd National Meeting (2017)

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