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Paper | Regular issue | Vol 60, No. 10, 2003, pp.2223-2230
Published online, 18th August, 2003
DOI: 10.3987/COM-03-9817
3-Hydroquinolylquinolines and Bisquinolyl-annelated Oxepin as Unexpected Products from the Reaction of p-Benzoquinone and N-Acetyl-1,4-dihydroquinolines

Andreas Hilgeroth* and Burkhardt Voigt

*Institute of Pharmaceutical Chemistry, Department of Pharmacy, Martin-Luther-University Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120 Halle, Germany


4-Substituted N-acyl-1,4-dihydroquinolines (1a, b) have been yielded by regioselective 4-arylation/alkylation via quinolinium intermediates. Acid-catalysed reaction of 1a, b with p-benzoquinone leads to unexpected 3-hydroquinolylquinolines (5a, b). The structure of compounds (5a, b) has been confirmed by spectroscopical data and additionally by formation of both O-acetyl derivatives (7a, b). Bisquinolyl-annelated oxepin (9a) was found as side product. Formation and stereochemistry of the spectroscopically characterized compound (9a) are discussed.