Abstract
Upon treatment of the pyridinium bromides 8a−c, obtained by quaternization of pyridines 7 with the allyl bromide 6, with base, the annulated methylene pyridoazepines 10a−c are formed. The reaction pathway includes base-catalysed propargyl-allene isomerization and dipole formation as the first steps followed by the ring closure of [9] to 10. The latter process represents the first example of the participation of an allene unit in 1,7-electrocyclization reactions of extended azomethine ylides. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
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