Three types of 2-alkenylthiazolines were designed and synthesized by a two-step method starting with 2-methylthiazoline and aromatic aldehydes, alkyl aldehydes and alkenyl aldehydes, respectively. Diels-Alder reactions of several 2-styryl-1,3-thiazolines with maleic anhydride in toluene were attempted. Expected Diels-Alder products were not observed or separated. Only starting materials were recovered. Several 2-alkenyl-1,3-thiazolines were successfully reacted with benzoyl chloride to form the N-benzoyl mono-substituted products. This is in sharp contrast with the di-benzoylation of 2-methylthiazoline reported previously by the Pittman group. 2-Methylbenzothiazole was reacted with different folds of aroyl chlorides. However, only di-aroylation products were observed even when a 1:1 2-methylbenzothiazole:aroyl chloride ratio was employed. Finally, N-methyl cyclic ketene N,O- and N,S-acetals were reacted with different alkylsulfonyl chlorides, respectively. Only di-substituted products were found in the N,O-acetal reacitons and only mono-substituted products were found in the N,S-acetal reactions even when different folds of sulfonyl chloride was employed.
| Identifer | oai:union.ndltd.org:MSSTATE/oai:scholarsjunction.msstate.edu:td-5187 |
| Date | 09 August 2008 |
| Creators | Guo, Hua |
| Publisher | Scholars Junction |
| Source Sets | Mississippi State University |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Theses and Dissertations |
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