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

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

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.

University of Southampton
Lamberto, Massimiliano
235abc6c-345f-41a5-a0c6-801c7932536c
Lamberto, Massimiliano
235abc6c-345f-41a5-a0c6-801c7932536c

Lamberto, Massimiliano (2003) Thiol mediated radical cyclisations of isocyanides : synthesis of N-heterocycles. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

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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Published date: 2003

Identifiers

Local EPrints ID: 465076
URI: http://eprints.soton.ac.uk/id/eprint/465076
PURE UUID: d75ee6a1-1ede-4a68-a593-62be85e9ffe5

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Date deposited: 05 Jul 2022 00:21
Last modified: 16 Mar 2024 19:56

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Author: Massimiliano Lamberto

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