Improved Enamine-type Addition of Dehydroaporphine Using Microwave Irradiation

CNU IR > Pharmacy and Science > 2011 Taiwanese-Russian Organic, Medicinal and Bio Chemistry Interactions & PST Medicinal Chemistry Symposium > Item 310902800/24236

Please use this identifier to cite or link to this item: https://ir.cnu.edu.tw/handle/310902800/24236

Title:	Improved Enamine-type Addition of Dehydroaporphine Using Microwave Irradiation
Authors:	Chih-Chiang Huang (黃志強) Shoei-sheng Lee (李水盛) Wei-Jan Huang (黃偉展)
Date:	2011
Issue Date:	2011-06-23 14:57:25 (UTC+8)
Abstract:	Previous report demonstrated that 7-substituted aporphine, possessing interesting biological aspects, could be synthesized via an enamine-type addition o of dehydroaporphine reacted with an electrophile, but it has the drawbacks of a long reaction time, low yield, and limitation to reactive electrophiles. Here we found that the reaction time and yield could greatly be improved under microwave irradiation in the presence of 4 equiv of sodium iodide for the synthesis of 7-benzyl dehydroglaucine. The application of this finding for treating dehydroglaucine with a variety of alkyl bromides also gave corresponding 7-substituted dehydroglaucines (2a-j) with yields of 14-89%. Other enamines such as 1,10-dimethoxydehydroaporphine (3a), 2,9-diacetyldehydroboldi (3b), and 7,8-dihydroberberine (5) were found to react with benzyl bromide under similar conditions as described above to give correyields, products (4a-b, 6) in satisfactory yields, indicating the versatility of this improved reaction condition.
Relation:	2011年台俄有機、藥物與生物化學交流暨藥物化學研討會，起迄日：2011/04/06~2011/04/05，地點：溪頭台大實驗林
Appears in Collections:	[Pharmacy and Science] 2011 Taiwanese-Russian Organic, Medicinal and Bio Chemistry Interactions & PST Medicinal Chemistry Symposium

Files in This Item:

File	Description	Size	Format
pp-20.pdf		73Kb	Adobe PDF	428	View/Open

Loading...