Chapter 1 contains a very brief overview of 3,3-disubstituted azetidinones. Also included in this chapter are the approaches to 'hybrid' azetidinones, i.e. those which contain the structural features of more than one class of azetidinones. Finally the target molecules for the present studies are listed. Chapter 2 contains details of use of various 2,3-dihydroxybutyric acid derivatives in enantioselective syntheses of 3-alkoxyazetidinones with an additional substituent at position 3. In chapter 3 similar studies on threonine derivatives for the syntheses of 3-amino-3-hydroxyethylazetidinones are described. These studies were only partially successful. In chapter 4 a systematic approach towards the syntheses of 3-alkoxyazetidinones is described. The steps involved were the formation of the C-3 carbanion from the parent azetidinones, reaction with acetaldehyde, oxidation of the resulting 3-alkoxy-3-hydroxyethylazetidinones and finally the reduction of the acetyl compound in a non-chelation controlled manner. It has been possible to synthesize protected 3-amino-3-hydroxyethylazetidinones by a similar series of reaction and the results are presented in chapter 5. Chapter 6 has details of syntheses of 3-hydroxy, 3-hydroxy-3-hydroxyethyl, 3-hydroxy-3-allyl and 3-$\sp\prime$epoxy$\sp\prime$azetidinones. Chapter 7 contains results of a detailed study on the impact of various variables on the non-chelation controlled reduction of 3-acylazetidinones (which have an additional substituent at 3-position). Chapter 8 is about the use of N, N-dimethylchloromethylenimnium chloride for the purpose of activating carboxylic acids for their final conversion to azetidinones. An attempt was made to determine the nature of the white solid obtained on reaction of DMF with oxalyl chloride, and the product of reaction between this white solid and a carboxylic acid.
| Identifer | oai:union.ndltd.org:uottawa.ca/oai:ruor.uottawa.ca:10393/5577 |
| Date | January 1990 |
| Creators | Sharma, Madan Kumar. |
| Contributors | Durst, Tony, |
| Publisher | University of Ottawa (Canada) |
| Source Sets | Université d’Ottawa |
| Detected Language | English |
| Type | Thesis |
| Format | 345 p. |
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