Improved enamine-type addition of dehydroaporphine using microwave irradiation

Wei J. Huang, Chih Chiang Huang, Ling W. Hsin, Yeun M. Tsai, Chin Ting Lin, Jung Hsin Lin, Shoei Sheng Lee

Research output: Contribution to journalArticle

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Abstract

Previous report demonstrated that 7-substituted aporphine, possessing interesting biological aspects, could be synthesized via an enamine-type addition 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-diacetyldehydroboldine (3b), and 7,8-dihydroberberine (5) were found to react with benzyl bromide under similar conditions as described above to give corresponding products (4a-b, 6) in satisfactory yields, indicating the versatility of this improved reaction condition.

Original languageEnglish
Pages (from-to)3062-3064
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number23
DOIs
Publication statusPublished - Jun 9 2010

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Sodium Iodide
Microwave irradiation
Microwaves
Bromides
benzyl bromide
dihydroberberine
aporphine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Huang, W. J., Huang, C. C., Hsin, L. W., Tsai, Y. M., Lin, C. T., Lin, J. H., & Lee, S. S. (2010). Improved enamine-type addition of dehydroaporphine using microwave irradiation. Tetrahedron Letters, 51(23), 3062-3064. https://doi.org/10.1016/j.tetlet.2010.04.008

Improved enamine-type addition of dehydroaporphine using microwave irradiation. / Huang, Wei J.; Huang, Chih Chiang; Hsin, Ling W.; Tsai, Yeun M.; Lin, Chin Ting; Lin, Jung Hsin; Lee, Shoei Sheng.

In: Tetrahedron Letters, Vol. 51, No. 23, 09.06.2010, p. 3062-3064.

Research output: Contribution to journalArticle

Huang, WJ, Huang, CC, Hsin, LW, Tsai, YM, Lin, CT, Lin, JH & Lee, SS 2010, 'Improved enamine-type addition of dehydroaporphine using microwave irradiation', Tetrahedron Letters, vol. 51, no. 23, pp. 3062-3064. https://doi.org/10.1016/j.tetlet.2010.04.008
Huang, Wei J. ; Huang, Chih Chiang ; Hsin, Ling W. ; Tsai, Yeun M. ; Lin, Chin Ting ; Lin, Jung Hsin ; Lee, Shoei Sheng. / Improved enamine-type addition of dehydroaporphine using microwave irradiation. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 23. pp. 3062-3064.
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