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Synthesis and Applications of Derivatives of 1,7-Diazaspiro[5.5

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Synthesis and Applications of Derivatives of 1,7-Diazaspiro[5.5 Synthesis and Applications of Derivatives of 1,7-Diazaspiro[5.5]undecane. A Thesis Submitted by Joshua J. P. Almond-Thynne In partial fulfilment of the requirements for the degree of Doctor of Philosophy Department of Chemistry Imperial College London South Kensington London, SW7 2AZ October 2017 1 Declaration of Originality I, Joshua Almond-Thynne, certify that the research described in this manuscript was carried out under the supervision of Professor Anthony G. M. Barrett, Imperial College London and Doctor Anastasios Polyzos, CSIRO, Australia. Except where specific reference is made to the contrary, it is original work produced by the author and neither the whole nor any part had been submitted before for a degree in any other institution Joshua Almond-Thynne October 2017 Copyright Declaration The copyright of this thesis rests with the author and is made available under a Creative Commons Attribution Non-Commercial No Derivatives licence. Researchers are free to copy, distribute or transmit the thesis on the condition that they attribute it, that they do not use it for commercial purposes and that they do not alter, transform or build upon it. For any reuse or redistribution, researchers must make clear to others the licence terms of this work. 2 Abstract Spiroaminals are an understudied class of heterocycle. Recently, the Barrett group reported a relatively mild approach to the most simple form of spiroaminal; 1,7-diazaspiro[5.5]undecane (I).i This thesis consists of the development of novel synthetic methodologies towards the spiroaminal moiety. The first part of this thesis focuses on the synthesis of aliphatic derivatives of I through a variety of methods from the classic Barrett approach which utilises lactam II, through to de novo bidirectional approaches which utilise diphosphate V and a key Horner-Wadsworth- Emmons reaction with aldehyde VI. The second part of this thesis concentrates on the synthesis of tetrahydrospirobiquinolines and their derivatives.ii The methodology developed utilises simple conditions, withstands a range of functional groups, and allows many substrates to be accessed under mild conditions. These compounds showed higher aminal stability relative to their aliphatic counterparts and were further derivatised by bromination, alkylation and cross-coupling techniques, all proceeding with the retention of the aminal centre. 3 The final part of this thesis details the attempts to complex these newly isolated compounds to a variety of elements across the periodic table, as well as initial investigations into their biological activities. i) Cordes, J.; Murray, P. R. D.; White, A. J. P.; Barrett, A. G. M. Org. Lett. 2013, 15 (19), 4992. ii) Almond-Thynne, J.; White, A. J. P.; Polyzos, A.; Rzepa, H. S.; Parsons, P. J.; Barrett, A. G. M. ACS Omega 2017, 2 (7), 3241 4 Acknowledgements First and foremost, I would like to thank my mentor Professor Tony Barrett. He has taught me an endless amount through my time as an MSci student through to my final days as a PhD student. I know I will continue to learn from him throughout my future career. Secondly, I thank Doctor Tash Polyzos, he was always ready to talk chemistry even though we were on the other side of the planet to each other. He made my time in Melbourne very enjoyable. I hope to get the chance to visit him, and his amazing group (of PCs) again. Professor Phil Parsons has become a very close friend to me. When I needed to talk to someone about anything at all, he was always there for me. I will miss working with him day to day but I am sure we will see a lot of each other in the future. Claire Weston gets my deepest thanks, from proof reading my illiterate gibberish, down to allowing me to talk at her about chemistry for hours on end whenever I needed to. I love you, even if you do not love chemistry anymore. I also extend my thanks for the huge number of academic staff that have helped me along the way, from casual chats through to helping me with various aspects of my project: Chris Cordier, Mark Crimmin, Virginia Manch, Andrew White, Henry Rzepa, Alan Spivey, Pete Haycock, Andrew Hughes, Don Craig, Chris Braddock, Alan Armstrong, Matt Fuchter and Lisa Haigh. Below are just a selection of people I have had the pleasure of working with, I appreciate them all for their help along the way; Robert Davidson, Alex “De Beers” Brown, Rosa Cookson, Sara Goldstein, Tsz “Freeman” Ma, Dan Elliott, Stefanie Reid, Lam Tran, Luiza Dos Reis Cruz, Hannah Cook, Jiaxu “Linda” Han, Alex Williams, Dan Jones, Taniya Zaman, Lewis Allen, Kath Fletcher, Kate Montgomery, Pete Blencowe, Laurianne Buisson, Milena Czyz, Timothy Connell, Martin Brzozowski, Dean van As, Nenad Micic, James Rushworth, and many, many more. 5 “There is scarcely any passion without struggle.” Albert Camus 6 Abbreviations 25 [α] D specific rotation Δ heat ΔG Gibbs free energy Å Angstrom (10-10 metres) Ac acetyl Acac acetylacetonate Ac2O acetic anhydride AIBN azobisisobutronitrile Anal. analysis Aq. aqueous Ar aryl Atm atmosphere (unit) Boc tert-Butyloxycarbonyl BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) Bn benzyl bp boiling point Bu butyl Bz benzoyl °C degrees Celsius cat. catalytic CI chemical ionisation conc. concentrated δ chemical shift d doublet DCC N,N’-dicyclohexylcarbodiimide dd doublet of doublet 7 ddd doublet of doublet of doublet DIBALH diisopropylaluminium hydride DIPEA N,N-diisopropylethylamine DMAP 4-dimethylaminopyridine DMF N,N-dimethylformamide DMP Dess-Martin periodinane DMSO dimethyl sulfoxide d.r diastereomeric ratio dt doublet of triplets dq doublet of quartets EDC 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide e.e enantiomeric excess EI electron ionization Elem. elemental equiv. equivalents ES electrospray Et ethyl h hour HBTU O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate HMDS bis(trimethylsilyl)amine HMPA hexamethylphosphoramide HPLC high-performance liquid chromatography Hz hertz i iso IBX 2-iodoxybenzoic acid IC50 half maximal inhibitory concentration IPA 2-propanol 8 IR infrared spectroscopy J coupling constant L litre LDA lithium diisopropylamine LED light emitting diode μ micro m multiplet m meta M molar Me methyl min minute(s) mL millilitre(s) mmol millimole(s) mol mole(s) Mpt melting point MS molecular sieves Ms mesylate NBS N-bromosuccinimide NIS N-iodosuccinimide NMR nuclear magnetic radiation Nu nucleophile o ortho PCC pyridinium chlorochromate PG general protecting group pH potential hydrogen Phth phthalimide Ph phenyl PMB 4-methoxybenzyl 9 ppm parts per million ppy 2-phenyl-pyridine PPTS pyridinium para-toluenesulfonate Pr propyl PTSA para-toluenesulfonic acid py pyridine q quartuplet R general substituent RCM ring-closing metathesis Rt room temperature s singlet SM starting material t or tert tertiary t triplet TBAF tetrabutylammonium fluoride TEMPO 2,2,6,6-tetramethylpiperidine 1-oxyl Tf trifluoromethanesulfonyl TFA trifluoroacetic acid THF tetrahydrofuran TIPS triisopropylsilyl TLC thin layer chromatography TMS trimethylsilyl TOF turnover frequency TON turnover number TS transition state UV ultra-violet light Vis visible spectrum light X halide or pseudohalide 10 Table of Contents Declaration of Originality ................................................................................................... 2 Copyright Declaration ......................................................................................................... 2 Abstract ............................................................................................................................... 3 Acknowledgements ............................................................................................................ 5 Abbreviations ...................................................................................................................... 7 Table of Contents .............................................................................................................. 11 1. General Introduction .................................................................................................. 16 1.1 Spirocyclic Compounds ........................................................................................ 16 1.2 Spiroketals ............................................................................................................ 17 1.3 Spirohemiaminals ................................................................................................. 20 1.4 Spiroaminals ......................................................................................................... 22 1.5 Aims of This Project .............................................................................................. 24 2. Aliphatic Derivatives of 1,7-Diazaspiro[5.5]undecane ............................................. 26 2.1 Previous Syntheses .............................................................................................. 26 2.1.1 Pre Barrett Group Syntheses ......................................................................... 26 2.1.2 The Barrett Synthesis ................................................................................... 27 2.1.3 Computational Investigations of Thiel ............................................................ 29 2.2 Lactam Synthesis ................................................................................................. 32 2.2.1 Altering Ring Sizes......................................................................................... 32 2.2.2 2-Substituted Lactams ..................................................................................
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