Next Article in Journal
Development of a Process for Separation of Mogroside V from Siraitia grosvenorii by Macroporous Resins
Previous Article in Journal
Use of Graphite Oxide and Graphene Oxide as Catalysts in the Synthesis of Dipyrromethane and Calix[4]pyrrole
Article Menu

Article Versions

Export Article

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

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

Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
Department of Biotechnology Engineering, Faculty of Engineering, International Islamic University Malaysia, 53100 Kuala Lumpur, Malaysia
Department of Pharmacognosy, Tokyo University of Pharmaceutical and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa-ku, Tokyo 142-8501, Japan
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)
Download PDF [922 KB, uploaded 18 June 2014]   |  


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).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top