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Abstract
This review provides a generalization of effective examples of 15N labeling followed by an analysis of 13C–15N (JCN) and 1H–15N (JHN) 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.
Highlights
Nitrogen heterocycles are a ubiquitous class of organic compounds that include azirine, azetidine, azole, azine and azepine derivatives and their fused analogs
The con rmation of the structure can be complicated by the azide–tetrazole equilibrium, ANRORC (Addition of Nucleophile, Ring Opening, Ring Closure) reaction, Dimroth rearrangement, etc., which are observed in the azolo and azine series under the action of nucleophilic reagents and solvents
The measurement of the 1H–15N and 13C–15N coupling constants allows the investigation of ring-chain tautomerism, the mechanisms of chemical transformation and other structural aspects of azoles, azines, azepines and their fused derivatives
Summary
Nitrogen heterocycles are a ubiquitous class of organic compounds that include azirine, azetidine, azole, azine and azepine derivatives and their fused analogs. The rst section describes the application of 1H–15N and 13C–15N constants for con rmation of the ways to fuse azole, azine and azepine rings during the synthesis of bicyclic, tricyclic and polycyclic compounds and the use of JHN and JCN in the studies of tautomeric rearrangements of heterocyclic derivatives. A combination of 15N-labeling and an analysis of JHN and JCN couplings is one of the approaches for the con rmation of the structure of a fused heterocyclic system that can be formed by different methods for the cyclization of an azole, azine or azepine ring to various ve- or six-membered heterocycles This method may be effective for the study of ring-chain tautomerisms that are observed in various classes of heterocycles. The weak 13C3–15N1 constant was used as an additional criterion for the con rmation of the structure of 25*
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