Improved Enamine-type Addition of Dehydroaporphine Using Microwave Irradiation

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標題:	Improved Enamine-type Addition of Dehydroaporphine Using Microwave Irradiation
作者:	Chih-Chiang Huang (黃志強) Shoei-sheng Lee (李水盛) Wei-Jan Huang (黃偉展)
日期:	2011
上傳時間:	2011-06-23 14:57:25 (UTC+8)
摘要:	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.
關聯:	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
顯示於類別:	[藥理學院] 2011年台俄有機、藥物與生物化學交流暨藥物化學研討會

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