Novel one-pot multi-bond forming reaction processes for the preparation of biologically active heterocycles

Sharif, Salaheddin Ahmad Ibrahim (2017) Novel one-pot multi-bond forming reaction processes for the preparation of biologically active heterocycles. PhD thesis, University of Glasgow.

Abstract

During the course of this PhD, a new one-pot thermal Overman rearrangement and ring-closing metathesis process was developed for the preparation of polycyclic compounds. In this method, commercially available phenols and anilines were converted to alkene derived allylic alcohols and then transformed via a one-pot process into 5-amino 2,5-dihydro-1-benzoxepines and 5-amino 2,5-dihydro-1H-benzazepines. The synthetic utility of these compounds was explored with the preparation of highly substituted hydroxylated analogues as well as a highly active hypotensive agent.

A novel one-pot process was also developed for the synthesis of allylic amide derived 2H-chromenes. The key substrates, propargyloxy cinnamyl alcohols were rapidly prepared from readily available salicylaldehydes. One-pot thermal Overman rearrangement of the corresponding allylic trichloroacetimidates, followed by a gold(I)-catalysed hydroarylation gave the 2H-chromenes in high yields. A mild chemoselective method for the oxidation of the 2H-chromenes to give coumarins was also discovered.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Overman rearrangement, ring-closing metathesis reaction, one-pot reaction process, 5-aminobenzoxepines, 5-aminobenzazepines, 2H-chromenes, coumarins.
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Sutherland, Dr. Andrew
• Date of Award: 2017
• Depositing User: Mr. S. A. I. Sharif
• Unique ID: glathesis:2017-8006
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 10 Mar 2017 13:51
• Last Modified: 01 May 2017 08:23
• URI: https://theses.gla.ac.uk/id/eprint/8006