Study on the Synthesis of 2-Substituted-5-ethoxycarbonyl-2H-azuleno[8,1-cd]pyridazine
| Autor: | Hong-Chang Chen, 陳宏昌 |
|---|---|
| Rok vydání: | 2008 |
| Druh dokumentu: | 學位論文 ; thesis |
| Popis: | 96 In thesis,the 5-ethylcarbonyl-2H-azuleno[8,1-cd]pyridazine have been synthesized,while the property was also discussed. The synthesis of 2-substituted-5-ethylcarbonyl-2H-azuleno[8,1-cd]pyridazine which have three methods. (a) Using the POCl3/DMF to proceed Vilsmeier-Haack reaction. (b) The reaction of 1-ethylcarbonyl-3-acetyl(or trifluroacetyl)-4-ethoxylazulene with phenyl hydrazine. (c) The reaction of 5-ethylcarbonyl-1H-azuleno[8,1-cd]pyridazine derivatives with methyl iodide to proceed alkylation. A comparison of 1HNMR observed for 2-substituted-5-ethylcarbonyl -2H- azuleno[8,1-cd]pyridazine with starting material, which is found that the 4,6,7,8,9-position of 2-substituted-5-ethylcarbonyl-2H-azuleno[8,1-cd] pyrida- zine chemical shift toward high fields. It was apparent that the property of 2-substituted-5-ethylcarbonyl-2H-azuleno[8,1-cd]pyridazine differs from the azulene derivatives in the past. 2-substituted-5-ethylcarbonyl-2H-azuleno[8,1-cd]pyridazine by POCl3/DMF as the Vilsmeier-Haack reaction reagent to synthesize 2-substituted- 5- ethyl- carbonyl- 4 or 7- formylazuleno[8,1-cd]pyridazine derivatives. The reaction of 5-ethylcarbonyl-1H-azuleno[8,1-cd]pyridazine derivatives with POCl3/DMF in high temperature to afford 5-ethylcarbonyl-1H-azuleno- 4-formyl[8,1-cd]pyridazine derivatives, while the reaction of 5-ethylcarbonyl- 1H-azuleno[8,1-cd]pyridazine and methyl vinyl ketone in acid condition give three products: 5-ethylcarbonyl-4-(3-oxo-propyl)-1H-azuleno[8,1-cd]pyridazine 24;5-ethylcarbonyl-2,4-(3-oxo-propyl)-2H-azuleno[8,1-cd]pyridazine25; 5-ethylcarbonyl-4,7-(3-oxo-propyl)-1H-azuleno[8,1-cd]pyridazine 26. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
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