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Communication | Regular issue | Vol 24, No. 10, 1986, pp.2797-2802
Published online, 1st January, 1970
DOI: 10.3987/R-1986-10-2797
Novel Approach to 1H-Benzo[f]pyrrolo[1,2-a]indole-5,10-diones

Eric O. M. Orlemans, Willem Verboom, and David N. Reinhoudt*

*Laboratory of Organic Chemistry, Twente University of Technology, Enschede, The Netherlands


The Friedel-Crafts reaction product of 1,4-dimethoxynaphthalene (3) and (S)-1-(trifluoroacetyl)-2-pyrrolidinecarbonyl chloride (4) could be converted in two steps into the benzo[f]pyrrolo[1,2-a]indole 10 following two different pathways. Compound 10 could easily be dehydrated using acid to 11. Upon reduction of 10 to the corresponding hydroquinone 12, spontaneous dehydration occurred.