Preparation of Novel Polycyclic
Heterocycles Using a Tin(II) Chloride Dihydrate-Mediated
Deacetalisation-Bicyclisation Sequence

Alex N. Cayley; Katherine A. Gallagher; Cécilia Ménard-Moyon; Jan Peter Schmidt; Louis J. Diorazio; Richard J. K. Taylor

doi:10.1055/s-0028-1083214

PAPER

Preparation of Novel Polycyclic Heterocycles Using a Tin(II) Chloride Dihydrate-Mediated Deacetalisation-Bicyclisation Sequence

Alex N. Cayley^a, Katherine A. Gallagher^a, Cécilia Ménard-Moyon^a, Jan Peter Schmidt^a, Louis J. Diorazio^b, Richard J. K. Taylor*^a
^a Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
Fax: +44(1904)434523; e-Mail: rjkt1@york.ac.uk;
^b AstraZeneca, Process Research & Development, Silk Road Business Park, Macclesfield, Cheshire SK10 2NA, UK

Abstract

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Abstract

Tin(II) chloride dihydrate-mediated deacetalisation-bicyclisation procedures for the construction of novel polycyclic heterocycles from amides possessing a pendant acetal group are reported. Optimisation and scoping studies are described; using this methodology, a range of known, and novel, ring-fused heterocyclic systems have been prepared, some in enantiomerically pure form.

Key words

heterocycles - tin(II) chloride dihydrate - deacetalisation - bicyclisation - tandem processes

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References

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