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Synlett 1994; 1994(7): 533-534
DOI: 10.1055/s-1994-22918
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A New Synthesis of Cyclopenta[a]phenanthrene Involving Cyclization of 2-(2-Naphthyl)-cyclopentylidenemalonodinitrile

Tadeusz Górecki* , Janusz J. Sepiol
  • *Department of Organic Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
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Publication Date:
18 September 2002 (online)

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16,17-Dihydro-15H-cyclopenta[a]phenanthrene (6) is synthesized in four steps by condensation of 2-(2-naphthyl)cyclopentanone (1) with malonodinitrile, cyclization of the cyclopentylidenemalonodinitrile 2 in concentrated sulfuric acid to 11-amino-16,17-dihydro-15H-cyclopenta[a]phenanthrene-12-carbonitrile (3), and the sequential removal of the nitrile and the amine functional groups from 3.