Advances in Organic Synthesis

Advances in Organic Synthesis

Volume: 11

Indexed in: Scopus, EBSCO, Ulrich's Periodicals Directory

Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. The series presents comprehensive reviews written by eminent ...
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Ring C–H Functionalization of Aromatic N-Oxides

Pp. 233-295 (63)

Rafał Loska

Abstract

Aromatic N-oxides occupy a central place in the synthesis of azine and azole derivatives. Unique reactivity of N-oxides makes them versatile substrates for introduction of various functional groups into the heterocyclic ring. The area of direct functionalization of C(sp2)–H bonds of aromatic N-oxides with various carbon and heteroatom substituents has seen renewed interest in recent years, resulting in introduction of several modern, versatile synthetic protocols into the arsenal of methods available within the chemistry of nitrogen heteroaromatic compounds. The aim of this review article is to provide an overview of these recent developments, together with an appropriate background in more classical N-oxide chemistry. It focuses on the most important reaction types characteristic for aromatic N-oxides, rather than the type of heterocyclic ring involved.

Keywords:

Aromatic compounds, Azines, Azoles, Cine Substitution, C–HActivation, Cross-Coupling, Cross-Dehydrogenative Coupling, Deoxygenation, Dipolar Cycloaddition, Imidazoles, Isoquinolines, Metalation, N-Oxides, Nitrogen Heterocycles, Nucleophilic Substitution, Oxazoles, Pyridines, Quinolines, Radical Substitution, Reaction Mechanisms, Thiazoles.

Affiliation:

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.