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Synthesis 1987; 1987(7): 641-645
DOI: 10.1055/s-1987-28033
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A Novel Two-Step Synthesis of Hexahydropyrazino[1,2-α]-quinolines

Walter H. N. Nijhuis* , Willem Verboom, David N. Reinhoudt
  • *Laboratory of Organic Chemistry, Twente University of Technology, P.O. Box 217, 7500 AE Enschede, The Netherlands
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Publication Date:
20 August 2002 (online)

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The hexahydropyrazino[1,2-a]quinolines 2 were prepared in good yields by reaction of 2-(4-substituted 1-piperazinyl)benzaldehydes 5 with malononitrile and subsequent thermal cyclization of the condensation products 6; the latter reaction takes place via a concerted [1,5] hydrogen transfer and subsequent ring closure by addition of a carbanion to the iminium double bond.

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