Studies on Peroxidation and Rearrangement Reactions toward the Synthesis of Heterocyclic Scaffolds under Batch/Continuous Flow

Abstract

The work presented in this thesis is related to organic synthesis and the development of novel methods for peroxidation, rearrangement reactions, and carbon-carbon (C-C), carbon-oxygen (C-O), and carbon-nitrogen (C-N) bond formation to synthesize various heterocyclic compounds. The thesis covers both batch and continuous flow techniques and aims to provide access to a diverse range of bioactive compounds, including commercial drugs and natural products. The key points presented in the thesis include: (a) Methods for peroxidation and rearrangement reactions: The thesis discussed various methods for performing peroxidation and rearrangement reactions to create heterocyclic scaffolds. These methods likely involve the introduction of peroxide groups into specific positions of molecules, followed by rearrangements to form complex heterocyclic structures.; (b) C-O bond formation via sp3-C-H peroxidation: One of the highlighted reactions involves the formation of carbon-oxygen (C-O) bonds through the peroxidation of sp3-hybridized carbon-hydrogen (C-H) bonds. This transformation likely involves the insertion of an oxygen atom from a peroxide source into a C-H bond, resulting in the creation of a C-O bond.; (c) Synthesis of heterocyclic compounds: This thesis developed the novel rearrangement of these peroxides to synthesize various heterocyclic bioactive compounds. Some examples of the synthesized compounds include (Z)-6-benzylidene-6H-benzo[c]chromene, dioxole-2-carboxamide, quinazolinone, and oxazoloquinazolinone. These compounds may have potential applications in the field of medicine and drug discovery due to their heterocyclic nature.; (d) C-C and C-N bond formation: This thesis also described the sequential transition-metal-free alkylative aromatization of tetralone using alcohol or amino alcohol as reactants. This transformation likely leads to the formation of carbon-carbon (C-C) and carbon-nitrogen (C-N) bonds, resulting in the synthesis of benzo[e/g]indole derivatives. Overall, the thesis presented a comprehensive exploration of various methods for peroxidation, rearrangement reactions, and carbon-carbon (C-C), carbon-oxygen (C-O), and carbon-nitrogen (C-N) bond formation to synthesize diverse heterocyclic compounds. The combination of batch and continuous flow techniques showcases the versatility and potential applications of these synthetic approaches in the creation of bioactive molecules with various pharmaceutical and industrial uses.