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Synfacts 2008(7): 0692-0692
DOI: 10.1055/s-2008-1078471
DOI: 10.1055/s-2008-1078471
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Indolo[3,2-a]carbazoles by Reaction of Indoles with 1,2-Diones
V. Nandialath, K. G. Abhilash, E. Suresh, V. Nair*
National Institute of Interdisciplinary Science and Technology, Trivandrum, India
Further Information
Publication History
Publication Date:
20 June 2008 (online)
Significance
Described here is an acid-catalyzed synthesis of indolo[3,2-a]carbazole derivatives by the condensation of indoles with 1,2-diones. Indolocarbazoles of type C were obtained when indoles were treated with benzil derivatives B while cyclobutene-1,2-diones D, upon treatment with indoles, gave indolocarbazoles E in good to high yields. Among other screened acid catalysts [AuCl3, Cu(OTf)3, Yb(OTf)3, SnCl4, Sc(OTf)3, BF3·OEt2], PTSA was found to be the best for this process. Reaction of indole with 2,3-butanedione gave a very low yield (12%) of C.