A novel hydantoin synthesis and exploration of related reactions

Chapter one gives a short history of the discovery of hydantoins, followed by their chemical properties and reactivity and concluding with the many ways to date that they have been synthesized.<br><br>In chapter two, a hydantoin compound RU58841, which is a popular anti-baldness agent is synthesized by an alternative pathway to those previously presented. The new synthesis gives 33% overall yield and avoids the hazardous reagent phosgene.<br><br>Chapter three explores the novel bromo–nitro substitution reaction. The reaction rate has been characterized by using a library of compounds and possible mechanisms for this reaction have been presented after consideration of the results of a Hammett plot.<br><br>In chapter four, another novel step from the alternative synthesis of RU58841 is explored. This reaction involves 2‑nitropropane as a leaving group to create an isocyanate intermediate which gives a hydantoin upon ring closure. Attempts and progress towards preparing isocyanate compounds using this method are discussed.<br><br>Chapter five summarizes the key findings and describes the future directions that can be taken with the new chemistry presented in this thesis.