Redox-Neutral Vicarious-Type Nucleophilic Amination of Heterocyclic N-Oxides with Organic Azides

Jeonghyun Min; Sujin Min; Eunjae Chung; Kyeongwon Moon; Hyung Sik Kim; Taejoo Jeong; Amitava Rakshit; Pargat Singh; Jung Su Park; In Su Kim

doi:10.1002/adsc.202400669

Redox-Neutral Vicarious-Type Nucleophilic Amination of Heterocyclic N-Oxides with Organic Azides

Jeonghyun Min
, Sujin Min
, Eunjae Chung
, Kyeongwon Moon
, Hyung Sik Kim
, Taejoo Jeong
, Amitava Rakshit
, Pargat Singh
, Jung Su Park
, In Su Kim

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	4158-4162
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	366
Issue number	19
DOIs	https://doi.org/10.1002/adsc.202400669
State	Published - 8 Oct 2024

Keywords

Amination
C−H functionalization
N-Heterocycles
Nucleophilic aromatic substitution
Organic azides

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10.1002/adsc.202400669

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title = "Redox-Neutral Vicarious-Type Nucleophilic Amination of Heterocyclic N-Oxides with Organic Azides",

abstract = "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.",

keywords = "Amination, C−H functionalization, N-Heterocycles, Nucleophilic aromatic substitution, Organic azides",

author = "Jeonghyun Min and Sujin Min and Eunjae Chung and Kyeongwon Moon and Kim, \{Hyung Sik\} and Taejoo Jeong and Amitava Rakshit and Pargat Singh and Park, \{Jung Su\} and Kim, \{In Su\}",

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doi = "10.1002/adsc.202400669",

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TY - JOUR

T1 - Redox-Neutral Vicarious-Type Nucleophilic Amination of Heterocyclic N-Oxides with Organic Azides

AU - Min, Jeonghyun

AU - Min, Sujin

AU - Chung, Eunjae

AU - Moon, Kyeongwon

AU - Kim, Hyung Sik

AU - Jeong, Taejoo

AU - Rakshit, Amitava

AU - Singh, Pargat

AU - Park, Jung Su

AU - Kim, In Su

PY - 2024/10/8

Y1 - 2024/10/8

N2 - 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.

AB - 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.

KW - Amination

KW - C−H functionalization

KW - N-Heterocycles

KW - Nucleophilic aromatic substitution

KW - Organic azides

UR - https://www.scopus.com/pages/publications/85200603013

U2 - 10.1002/adsc.202400669

DO - 10.1002/adsc.202400669

M3 - Article

AN - SCOPUS:85200603013

SN - 1615-4150

VL - 366

SP - 4158

EP - 4162

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 19

ER -

Redox-Neutral Vicarious-Type Nucleophilic Amination of Heterocyclic N-Oxides with Organic Azides

Abstract

Keywords

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