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Molecules 2011, 16(9), 7267-7287; doi:10.3390/molecules16097267

Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: The Amide Question

1, 1, 1, 2, 3, 4, 5 and 1,*
1 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia 2 Department of Biotechnology Engineering, Faculty of Engineering, International Islamic University Malaysia, 53100 Kuala Lumpur, Malaysia 3 Department of Pharmacognosy, Tokyo University of Pharmaceutical and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan 4 Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa-ku, Tokyo 142-8501, Japan 5 Environmental and Bioprocess Technology Centre, SIRIM Berhad, 40000 Shah Alam, Malaysia
* Author to whom correspondence should be addressed.
Received: 5 August 2011 / Revised: 16 August 2011 / Accepted: 17 August 2011 / Published: 25 August 2011
(This article belongs to the Section Organic Synthesis)
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The n-butyramido, isobutyramido, benzamido, and furancarboxamido functions profoundly modulate the electronics of the stilbene olefinic and NH groups and the corresponding radical cations in ways that influence the efficiency of the cyclization due presumably to conformational and stereoelectronic factors. For example, isobutyramido- stilbene undergoes FeCl3 promoted cyclization to produce only indoline, while n-butyramidostilbene, under the same conditions, produces both indoline and bisindoline.
Keywords: stilbene; indoline; bisindoline; FeCl3 stilbene; indoline; bisindoline; FeCl3
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Kee, C.H.; Ariffin, A.; Awang, K.; Noorbatcha, I.; Takeya, K.; Morita, H.; Lim, C.G.; Thomas, N.F. Cyclization vs. Cyclization/Dimerization in o-Amidostilbene Radical Cation Cascade Reactions: The Amide Question. Molecules 2011, 16, 7267-7287.

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