Abstract
This thesis details efforts to apply the recently formalised dipole-transmissive 1,3-dipolar cycloaddition (DTDC) reaction to create structurally diverse ring architectures. Cycloadditions are a highly efficient technique as they construct multiple carbon bonds in a one pot procedure. The diene-transmissive Diels-Alder (DTDA) is an elegant extension to this as it is an excellent technique in the synthesis of fused 6-membered ring systems while displaying high selectivity and versatility. The seamless blend of the principles of the DTDA with the 1,3-dipolar cycloaddition (1,3-DC), opens a doorway to wide chemical space. The DTDC is particularly powerful as it displays high chemo-, regio- and stereoselectivity while being highly economical and versatile.
Chapter 2 describes the application of the DTDC to generate six 2-pyrazolines, which are a known medicinally privileged scaffold. However, unfortunately no sign of antibacterial activity was observed.
Chapter 3 showcases the second aim of the project which explored divergent reactivity. Specifically, α-diazo phenyl containing compounds were synthesized and shown to subsequently afford aziridines and anthranils. Preliminary work suggests these compounds are proceeding via a nitrene intermediate.