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Avcil, Muhammet (2013)
Languages: English
Types: Doctoral thesis
Subjects: QD0241
[For full abstract, with illustrations, see pdf file].\ud \ud Part 1. Concise Synthesis of Highly Substituted Isoquinolin-1(2H)-ones via IMDA\ud The primary goal of this DPhil research project was to further investigate the mechanism of a novel thermally activated cyclisation reaction discovered within the Parsons’ research group.\ud Through the synthesis and cyclisation of the substituted pyrrole rings 2.38a-c we have\ud investigated the mechanism and increased the scope of the cyclisation reaction.\ud \ud We have also developed a robust route to advanced intermediate 2.10 in the synthesis of\ud hymenialdisine 2.1.\ud \ud Part 2. Investigation and Development of a Novel Cascade Reaction\ud The aim of this DPhil research project was to devise and execute a series of experiments to gain a better mechanistic understanding of the novel thermal cyclisation, discovered within the Parsons’ research group. To further investigate the mechanism and scope of the\ud cyclisation, the model system 2.1 was initially selected.\ud \ud Through extensive modification and manipulation of the cyclisation precursor 2.1, we have\ud increased the scope of the cyclisation and postulated a reaction pathway. During these studies remarkable transformation of ketone 2.81 to alkyne 2.82 was also observed.\ud The repeatability of the above reactions was also investigated by synthesising various\ud analogues.
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    • Synthesis of Acyl Chloride 2.24
    • Amide Coupling
    • Investigation into the Role of LiI in the Cyclisation
    • Proposed Mechanisms for the Cyclisation
    • 2.3. Synthesis of Various Diels-Alder Products
    • 2.3.1. Synthesis of Ethyl Substituted Coupling Precursor 2.37a
    • 2.3.2. Synthesis of Coupling Precursors 2.37b-c
    • 2.3.3. Synthesis of Cyclisation Precursors 2.38a-c
    • 2.3.4. Thermal Cyclisations
    • 2.4. New Route for the Synthesis of Carboxylic Acid 2.10
    • 2.4.1. Outline of Investigation
    • 2.4.2. Synthesis of Carboxylic Acid 2.10 3. Conclusion and Future Work 4. Experimental Section
    • 4.1. General Procedure
    • 4.2. Compounds
    • But-3-yn-1-yl 4-methylbenzenesulfonate (2.18)
    • N-(4-Methoxybenzyl)but-3-yn-1-amine (2.19)
    • tert-Butyl but-3-yn-1-yl(4-methoxybenzyl)carbamate (2.20)
    • Ethyl 5-((tert-butoxycarbonyl)(4-methoxybenzyl)amino)pent-2-ynoate (2.21)
    • Ethyl 5-((4-methoxybenzyl)amino)pent-2-ynoate hydrochloride (2.22)
    • 1-(Phenylsulfonyl)-1H-pyrrole-2-carbonyl chloride (2.24)
    • Ethyl-5-(N-(4-methoxybenzyl)-1-(phenylsulfonyl)-1H-pyrrole-2-carboxamido)
    • pent -2-ynoate (2.8)
    • Ethyl 2-(4-methoxybenzyl)-1-oxo-1,2-dihydroisoquinoline-5-carboxylate (2.11)
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