Copper Catalyzed Synthesis of Five and Six Membered Nitrogen Containing Heterocycles

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The contents of this thesis have been divided into five chapters based on the results of experimental works performed during the complete course of the research period. Chapter I of the thesis describes the importance of various nitrogen heterocyclic scaffolds and different copper catalyzed strategies for their synthesis. All the other chapters deals with copper catalyzed C−C, C−N and C−O bond forming reactions leading to various nitrogenous heterocycles. Chapter II A demonstrates a copper catalyzed method for the synthesis of 3-aroylindoles via sp3 C−H bond functionalization of o-alknylated amine through C−C and C−O bond formation. Chapter II B describes a metal free cascade synthesis of 3-aroylindoles from o-alkynyl amine precursors via sp3 C−H bond functionalization. Chapter III illustrates a Cu catalyzed route to indoloquinoxaline-6-ones starting from o-indolyl-N,N-dimethylarylamines through an intramolecular oxidative coupling pathway. Chapter IV portrays the synthesis of 3- methyleneisoindolin-1-ones from aryl alkynyl acids and 2-halobenzamides which proceeds via decarboxylative cross-coupling / 5-exo-dig heteroannulation process. Chapter V describes a copper catalyzed protocol for the syntheses of 4,5-disubstituted-1,2,4-triazole-3-thiones and 4,5- disubstituted-1,2,4-triazoles from N-arylidenearylthiosemicarbazides via an intramolecular C−N bond formation at the imine C−H bond followed by a desulfurization.
Supervisor: Bhisma K. Patel