Redox-Neutral Vicarious-Type Nucleophilic Amination of Heterocyclic N-Oxides with Organic Azides,Advanced Synthesis & Catalysis

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Redox-Neutral Vicarious-Type Nucleophilic Amination of Heterocyclic N-Oxides with Organic Azides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-07-10 , DOI: 10.1002/adsc.202400669
Jeonghyun Min ₁ , Sujin Min ₁ , Eunjae Chung ₁ , Kyeongwon Moon ₁ , Hyung Sik Kim ₁ , Taejoo Jeong ₁ , AMITAVA RAKSHIT ₁ , Pargat Singh ₁ , Jung Su Park ₂ , In Su Kim ₁

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Site-selective amination of N-heterocycles is an interesting topic in organic synthesis and drug discovery. We herein present a method for the vicarious-type nucleophilic amination of azine N-oxides and cyclic iminoamides using iminyl anions, readily generated from organic azides under basic conditions. The plausible reaction mechanism involving nucleophilic aromatic substitution by iminyl anions is elucidated by a series of mechanistic investigations.

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