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Novel One-Pot Syntheses of Uracils and Arylidenehydantoins, and Analysis of Xylitol in Chewing Gum by Gc-Ms

The first section of this dissertation (Chapter I-III) describes the development of new methodologies to prepare uracil and arylidenehydantoin derivatives. A regioselective synthesis of 6-alkyl- and 6-aryluracils was developed by the dimerization of 3-alkyl- and 3-aryl-2-propynamides promoted by either Cs2CO3 or K3PO4. A range of 3-aryl-2- propynamides, with both electron-deficient and electron-rich 3-aryl substituents, were successfully reacted in high yields. A synthetic route to prepare arylidenehydantoins was developed using the Pd-catalyzed dimerization of 3-aryl-2-propynamides. Both electron rich and electron deficient 3-aryl-2-propynamides were dimerized successfully to produce the desired arylidenehydantoins in moderate to excellent yields. The second section of this dissertation (Chapter IV and V) describes the development of a reliable low-cost method to determine amounts of xylitol in sugar free gum samples to predict dangerous exposure levels for dogs. Xylitol is generally considered safe for human consumption and is frequently used in sugar free gum, however, it is extremely toxic to dogs. It is unknown if partially consumed chewing gum is also dangerous. A method to determine xylitol content of these sugar free gum samples employing GC-MS with direct aqueous injection (DAI) is presented. This method was successfully applied to over 120 samples including, fresh gum, 5 min, 15 min, and 30 min chewed gum samples. Further extension of this work resulted in the development of an undergraduate laboratory experiment for upper-level undergraduate chemistry students which teaches calibration methods, xylitol extraction, sample preparation for GC-MS analysis, and data analysis.

Identiferoai:union.ndltd.org:MSSTATE/oai:scholarsjunction.msstate.edu:td-4315
Date06 May 2017
CreatorsRajapaksha, RM Suranga Mahesh
PublisherScholars Junction
Source SetsMississippi State University
Detected LanguageEnglish
Typetext
Formatapplication/pdf
SourceTheses and Dissertations

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