This thesis describes the chemistry developed during a study of novel transition metal-catalysed reactions. Chapter 2 describes a novel procedure for the synthesis of 2,5-disubstituted furans via the isomerisation of 1,4-alkyne diols, avoiding the pitfalls of the traditional Paal-Knorr reaction. The initial ruthenium catalysed isomerisation is followed by an in situ cyclocondensation reaction using an acid co-catalyst in a one step route to furan derivatives. In addition the synthesis of the 1,4-dicarbonyl surrogates, 1,4-alkyne diols, is detailed. The methodology detailed in chapter 2 is then used in the synthesis of pyrrole derivatives in Chapter 3. Replacement of the acid co-catalyst with 2 equivalents of amine allow various pyrrole derivatives to be synthesised using the 1,4-alkynediols as starting materials. Various amines can also be used from anilines, benzylamines and aliphatic amines, allowing access to a wide range of products.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:501617 |
| Date | January 2009 |
| Creators | Pridmore, Simon J. |
| Contributors | Williams, Jonathan |
| Publisher | University of Bath |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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