The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline

Ariffin, Azhar and Hadi, A.H.A. and Thomas, N.F. and Kee, C.H. and Awang, Khalijah and Weber, J.F.F. and Lim, C.G. and Mukhtar, M.R. (2008) The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline. Heterocycles, 75 (5). pp. 1097-1108. ISSN 0385-5414

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Abstract

The addition of benzophenone to a FeCl(3)/CH(2)Cl(2) mixture in the presence of 3',4'-dimethoxy-2-acetamidostilbene 17 unexpectedly leads to a dramatic improvement in yield of the indoline 20 from 38% (previously reported by us) to 75.4%, after careful examination of a variety of reaction conditions. A catalytic cycle has been proposed that involves not only stilbene radical cations but also Fe(2+) promoted benzophenone ketyl radical formation which enhances cyclisation, suppresses dimerization and accounts for the virtually quantitative recovery of the benzophenone.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: radical cation, benzophenone, ketyl radical, maleic anhydride, oxidative cyclization, fecl3-promoted synthesis, alkaloids, derivatives, construction, dimerization, duocarmycins, cc-1065
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 02:32
Last Modified: 01 Mar 2019 09:05
URI: http://eprints.um.edu.my/id/eprint/8070

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