Formation of Heterocyclic Ring on Amino-substituted Naphthoquinone via Palladium Catalyzed C-H Activation
| Autor: | Yu-Jen Chiu, 邱郁仁 |
|---|---|
| Rok vydání: | 2019 |
| Druh dokumentu: | 學位論文 ; thesis |
| Popis: | 107 In this study, several nitrogen-containing naphthoquinone heterocyclic compounds, 4-6, were prepared from naphthoquinone derivatives 1-3c. The reactions were carried out in an open air system and in the presence of Pd(OAc)2 as the catalyst. Firstly, compound 4 was prepared from 1 with cyclohexylamine and in the yield of about 20%. Its crystal structure is resolved via single crystal X-ray determining methods. Obviously, a cyclization process took place during the reaction. Next, two amination products 2_a and 2_b were produced through the reaction of 2 with triethylamine. The reaction was carried out under inert gas (N2) system and in the presence of Pd(OAc)2 as the catalyst. The crystal structure of 2_a was determined as well. In this reaction, the desired compound with expected spiro structure was not observed although several different bases had been attempted to achieve the goal. Later, two amination products 3a_a and 3b_b were yielded through the reactions of cyclohexylamine with 3a and 3b, respectively, under inert gas (N2) system and in the presence of Pd(OAc)2 as the catalyst. The crystal structures of both 3a_a and 3b_a were determined as well. Rather similar structure features were shown for both compounds. Finally, the reaction of cyclohexylamine with 3c under similar reaction condition produced several unexpected products, 5, 6 and 7. The crystal structures of 5 and 6 were determined except 7. The conformation of 7 remains unknown. There is one more product 3c_a was observed. Judging from its crystal structure, it is obviously a product of Heck reaction. A mechanism was proposed to accommodate the processes for the formations of all compounds. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
| Externí odkaz: |
|