Synthesis of 15N-labeled heterocycles via the cleavage of C-N bonds of anilines and glycine-15N

Jiwen He; Xingguo Zhang; Qiuqin He; Hao Guo; Renhua Fan

doi:10.1039/d1cc01734a

Synthesis of ¹⁵N-labeled heterocycles via the cleavage of C-N bonds of anilines and glycine-¹⁵N

Chem Commun (Camb). 2021 Jun 1;57(44):5442-5445. doi: 10.1039/d1cc01734a.

Authors

Jiwen He¹, Xingguo Zhang², Qiuqin He³, Hao Guo⁴, Renhua Fan³

Affiliations

¹ Academy for Engineering and Technology, Fudan University, 220 Handan Road, Shanghai 200433, China.
² College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
³ Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, China.
⁴ Academy for Engineering and Technology, Fudan University, 220 Handan Road, Shanghai 200433, China and Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, China.

PMID: 33949517
DOI: 10.1039/d1cc01734a

Abstract

A nitrogen replacement process that directly incorporates the 15N atom of glycine-15N into anilines was reported. The process involves a Csp2-N bond cleavage of anilines driven by dearomatization and a Csp3-N bond cleavage of glycine-15N driven by aromatization. A variety of 15N-labeled aromatic heterocycles can be prepared via this process.

MeSH terms

Aniline Compounds / chemistry*
Glycine / chemistry*
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry
Hydrocarbons, Aromatic / chemical synthesis*
Hydrocarbons, Aromatic / chemistry
Molecular Structure
Nitrogen Isotopes

Substances

Aniline Compounds
Heterocyclic Compounds
Hydrocarbons, Aromatic
Nitrogen Isotopes
Nitrogen-15
Glycine