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Updated: May 6, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Synthesis of polyhydroxylated quinolizidines and azaspiro[4.5]decanes from D-xylose
Michał Malik1, Grzegorz Witkowski, Magdalena Ceborska
1Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland, and Institute of Physical Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
Abstract:
The synthesis of novel polyhydroxylated quinolizidines and azaspiro[4.5]decanes is reported. A key step of this transformation involved an addition of allylmagnesium bromide to an ω-bromonitrile derived from D-xylose followed by an intramolecular displacement of a bromide. The resulting cyclic imine was treated either with allylmagnesium bromide or with NaBH4, to provide 2,2-diallyl- or 2-allylpiperidine, respectively. The desired bicyclic framework was constructed via a ring-closing metathesis reaction. The Ru catalysts were reused in the following syn-dihydroxylation step.
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