Metal and oxidant free direct C(sp3)-H arylation of N-heterocycles

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The contents of the thesis entitled “Metal and Oxidant Free Direct C(sp3)-H Arylation of N-heterocycles” have been divided into six chapters based on the results of experimental works performed during the complete course of the research period. Carbon–hydrogen bonds are abundant in most organic molecules. Methods for their direct and selective functionalization are attractive as an efficient means to access more complex molecular structure. The first chapter of the thesis presents a review on different aspects of C-H arylation of secondary amines. Chapters 2-4 describes the studies on the metal and oxidant free direct C(sp3)-H arylation of N-heterocycles (e.g. pyrrolidine, substituted pyrrolidines, 1,2,3,4-tetrahydroisoquinoline and β-carbolines). Chapter 2 describes metal and oxidant free route to direct C(sp3)-H arylation of pyrrolidine. In Chapter 3, a regio-, diastereo and enantiospecific metal free C(sp3)-H arylation of 2-substitued pyrrolidines has been described. The method was found to be efficient for the synthesis of optically active 5-aryl-2,5-disubstituted pyrrolidine. Chapter 4 describes direct C-H arylation of 1,2,3,4-tetrahydroisoquinoline and β-carbolines under metal, oxidant, and solvent free conditions. C-H functionalization enabled stereoselective Ugi-azide reaction of N-heterocycles to α-tetrazolyl alicyclic amines has been described in chapter 5. Finally, Chapter 6 contain the copies of 1H, 13C NMR spectra, and HPLC chromatogram, of selected new compounds respectively.
Supervisor: Chandan K. Jana