15N labeling and analysis of 13C-15N and 1H-15N couplings in studies of the structures and chemical transformations of nitrogen heterocycles

Sergey L Deev; Igor A Khalymbadzha; Tatyana S Shestakova; Valery N Charushin; Oleg N Chupakhin

doi:10.1039/c9ra04825a

¹⁵N labeling and analysis of ¹³C-¹⁵N and ¹H-¹⁵N couplings in studies of the structures and chemical transformations of nitrogen heterocycles

RSC Adv. 2019 Aug 28;9(46):26856-26879. doi: 10.1039/c9ra04825a. eCollection 2019 Aug 23.

Authors

Sergey L Deev^{1

2}, Igor A Khalymbadzha¹, Tatyana S Shestakova¹, Valery N Charushin^{1

2}, Oleg N Chupakhin^{1

2}

Affiliations

¹ Ural Federal University 19 Mira Street 620002 Yekaterinburg Russian Federation deevsl@yandex.ru.
² I. Ya. Postovsky Institute of Organic Synthesis 22 S. Kovalevskoy Street 620219 Yekaterinburg Russian Federation.

Abstract

This review provides a generalization of effective examples of ¹⁵N labeling followed by an analysis of ¹³C-¹⁵N (J _CN) and ¹H-¹⁵N (J _HN) coupling constants in solution as a tool to study the structural aspects and pathways of chemical transformations (e.g., rearrangements and ring-chain tautomerisms) in monocyclic and fused nitrogen heterocycles. This approach allows us to significantly expand and supplement the scope of NMR techniques for heterocyclic compounds. Moreover, methods for the incorporation of ¹⁵N atoms into the cores of various N-heterocycles have been collected in this work.

Publication types

Review