Amine Oxidase Inspired Catalysis: Application towards the Synthesis of Olefins and N-Heteroarenes

Ramdas, Thorve Pradip (2023) Amine Oxidase Inspired Catalysis: Application towards the Synthesis of Olefins and N-Heteroarenes. PhD thesis, Indian Institute of Science Education and Research Kolkata.

Text (PhD thesis of Thorve Pradip Ramdas (17RS063)) 17RS063.pdf - Submitted Version Restricted to Repository staff only Download (42MB)

Abstract

Modern synthetic chemistry has prevailed to provide novel approaches to structural frameworks for drug molecules, agrochemicals, and other essential components of the living being. This thesis discusses developing and utilizing amine oxidase-inspired quinone catalysts for various organic transformations. These initial findings motivated me to synthesize more economical, easily handleable, and air-friendly catalyst systems with comparable efficiency. This thesis is divided into five chapters which are briefly discussed below: Chapter 1. Amine Oxidase Inspired Catalysis: History, Development, and Application in Organic Transformation This chapter briefly discusses amine oxidase-inspired catalyst, the development of coenzyme mimic-inspired catalyst, and its application in various C–C and C–X (X = heteroatom) bond formation reactions through the dehydrogenation of amine methodology. Modern organic chemists have lately started using imine as an intermediate in various organic transformation reactions under this Schiff base intermediate approach. According to the prior literature review, very few reports of heteroarene and olefin molecule synthesis using sustainable quinone-based catalyst systems. Chapter 2. Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase- Inspired Catalyst Under Ambient Air This chapter describes the biomimetic ortho-quinone co-factor catalyzed (E)-selective deaminative disubstituted olefination of various primary amines with dehydrogenation of heteroarenes, including pyrimidines, pyridines, pyrazines, pyridazines, quinolines, quinoxalines, 1-benzyl benzo-imidazole, benzoxazoles, benzothiazoles, and triazines under ambient air. This study demonstrated the first finding of benzylic deaminative (E)-selective olefination with various electron-deficient heteroarenes. Chapter 3. Aerobic Primary and Secondary Amine Oxidation Cascade by a Copper Amine Oxidase-Inspired Catalyst This chapter manifests the bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and an in situ-generated non-native secondary amine. The catalyst consists of an ortho-quinone co-factor phd and a copper ion and operates under ambient aerial conditions. Chapter 4. Construction of 1,2,4-triazole-fused heterocycles via an amine oxidaseinspired catalyst This chapter is to develop the regioselective synthesis of 1,2,4-triazoles utilizing an amine oxidase-inspired catalysis. An ortho-quino-enzyme mimic 1,10-phenanthroline-5,6- dione (phd) catalyzed the coupling of two readily available nucleophilic components, primary amine, and hydrazine, in the presence of a Lewis acid (FeCl3) as a co-catalyst using oxygen (1 atm) as the terminal oxidant. Chapter 5. Synthesis of furo-/ thieno quinoline compounds using amine oxidase-inspired catalyst This chapter describes the applications of bio-inspired ortho-quinone catalysis for synthesizing furo-/ thieno quinolines that are prevalent in various bioactive molecules. The reaction involved a complex cascade of primary amine dehydrogenation, acid-catalyzed transamination, cyclization, and secondary amine dehydrogenation.

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