A systematic study was carried out for the synthesis of aziridine 2-phosphonates by using two methods. First method is the classical Gabriel-Cromwell reaction and the second one is the modified version of Gabriel-Cromwell reaction which was developed in this thesis. In the first method, vinyl phosphonate was used as the starting material, then it was brominated to get 1,2-dibromoethyl phosphonate. HBr elimination from this compound, then reaction with different primary amines gave
desired aziridinyl phosphonates in good yields. In the second method, easily available acetyl phosphonate was used as the starting material which was reacted with DBU and tosyl chloride to get &alpha / -tosylated vinyl phosphonate. Reaction of this compound with the same amines gave aziridinyl phosphonates in good yields, as well. Biological activities of all newly synthesized compounds were studied against different bacteria.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/12612595/index.pdf |
| Date | 01 October 2010 |
| Creators | Babiz, Hakan |
| Contributors | Dogan, Ozdemir |
| Publisher | METU |
| Source Sets | Middle East Technical Univ. |
| Language | English |
| Detected Language | English |
| Type | M.S. Thesis |
| Format | text/pdf |
| Rights | To liberate the content for public access |
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