The recyclization of derivatives of 2-aryl-5-benzylfuran containing a tosylamine fragment to give indoles has been studied. If the tosylamino group is in the ortho position of the aryl substituent, the recyclization proceeds such that the furan ring may be seen as a formal equivalent of a 1,3-diketone. If, on the other hand, the tosylamino group is in the ortho positions of both the aryl and benzyl substituents, the recyclization proceeds through a pathway, in which the furan ring acts as the equivalent of a 1,4-dicarbonyl compound.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 376-382, March, 2009.
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Pilipenko, A.S., Gaidarzhi, A.N. & Butin, A.V. Recyclization of tosylamino derivatives of 2-aryl-5-benzylfuran to give indoles through two alternative pathways. Chem Heterocycl Comp 45, 302–307 (2009). https://doi.org/10.1007/s10593-009-0274-y
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DOI: https://doi.org/10.1007/s10593-009-0274-y