Study on Addition Reaction of 3,4-Dihydroisoquinolines with γ-Hydroxy-α,β-unsaturated Phenyl Ketone at Room Temperature
| Autor: | Li, Deng-Hong, 李登鴻 |
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| Rok vydání: | 2016 |
| Druh dokumentu: | 學位論文 ; thesis |
| Popis: | 104 The application of asymmetric aza-Michael addition reactions by utilizing organic catalyst is one of the important synthesis methods to create a carbon-nitrogen bond. And it is useful for nature product and medicine synthesis. It has economic benefits and is environmentaly friendly in asymmetric synthesis. In this thesis, aza-Michael addition reaction’s product is 1,3-oxazolidine. 1,3-Oxazolidines are important structural moieties that exist in many biologically active compound. For example, quinocarcin and its analogue terazomine are polycyclic tetrahydroisoquinoline alkaloids with remarkable activities against several tumor cell lines. Therefore, we synthesised the new type of organocatalysts 59、60 containing camphor derived [3.2.1] bicyclic thiourea has also been designed and prepared. It shows low [α]D values to cyclize 3,4-dihydroisoquinolines and γ-hydroxy-α,β-unsaturated phenyl ketone. But, the cyclization took only 15 min at room temperature without any catalyst and addition agent. Then, we examined a wide variety of 3,4-dihydroisoquinolines substates. The results showed that the reaction tolerated both electron-donating and –withdrawing groups at the various positions on the phenyl ring of 3,4-dihydroisoquinolines. The reaction provides the various products in good to excellent yields (82-98%). |
| Databáze: | Networked Digital Library of Theses & Dissertations |
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