Thiol mediated radical cyclisations of isocyanides : synthesis of N-heterocycles

Abstract

This thesis is concerned with the synthesis and radical cyclisations of alkenyl and alkynl isocyanides with thiols. Special interest is given to developing a fast and efficient synthetic route to functionalised N-heterocycles and polycylic systems.

Chapter 2 describes the synthesis of simple alkenyl isocyanides and their radical cyclisations, mediated by thiols, to access pyrrolines and pyroglutamates.  Radical cyclisations of alkenyl isocyanides were also investigated on solid phase.

Chapter 3 describes the synthesis of functionalised alkenyl and alkynyl isocyanides and their thiol mediated radical cyclisations promoted by microwave irradiation. The microwave assisted radical cyclisations were found to proceed in good to excellent yields in very short time, compared to traditional thermal heating techniques.

Chapter 4 reports the investigation into the synthesis of polycyclic systems via a novel radical cyclisation/N-alkylation/ring closing metathesis strategy, starting from simple bis-alkenyl isocyanides. Several indolizidines and bicyclic lactams were successfully synthesised.  Tricyclic indolizindines were also accessed via Pauson-Khand reaction of functionalised pyroglutamates in good yields.

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