C-H Aminations and Syntheses of Heterocycles Using Nitrosoarene

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Selective transformation of ubiquitous but inert C-H bonds into C-C, C-N, C-O, C-X is the central interest to modern organic chemistry. Direct transformation of C-H bond into C-N bond has been emerged as a high impact area of research, because it allows the preparation of nitrogen-containing cyclic and acyclic compounds which are biologically active or which can act as synthetic scaffolds for pharmaceuticals. The contents of this thesis entitled “C-H Aminations and Syntheses of Heterocycles Using Nitrosoarene” have been divided into six chapters. The first chapter of the thesis provides a review on different aspects of C-H amination with various aminating agents. All the other chapters describe the C-N bond forming reactions of nitrosoarenes. Chapter 2 describes C(sp2)-H arylamination of 2-hydroxyarene to provide 2-hydroxy-di(het)aryl amines. Chapter 3 illustrates C(sp3)-H functionalization enabled annulation of nitrosoarenes and N-heterocycles to ring-fused imidazoles. Selective N-terminal proline modification of peptides via amino-oxazole synthesis and application of modified peptides in cell imaging have been described in chapter 4. Chapter 5 demonstrates indole synthesis via C(sp2)-H functionalization of nitrosoarene and β-C(sp3)-H functionalization of secondary amines. Finally, chapter 6 contains copies of 1H and 13C NMR spectra.
Supervisor: Chandan K. Jana