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Updated: Aug 9, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
A diastereoselective radical cyclization approach to substituted quinuclidines
Thomas A Hunt1, Andrew F Parsons, Robert Pratt
1Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
Abstract:
A new, concise, and flexible approach to novel quinuclidines has been developed, which employs a phosphorus hydride mediated radical addition/cyclization reaction in the key step. 1,7-Diene 5 reacts with diethyl thiophosphite in an efficient and diastereoselective radical addition/cyclization reaction to give trisubstituted piperidines 4ab. Piperidines 4ab are subsequently converted into 2,5-disubstituted quinuclidines using S(N)2-type cyclizations. Finally, the resulting quinuclidines are shown to undergo novel Horner-Wadsworth-Emmons-type (HWE-type) reactions to give unsaturated quinuclidines 21a and 21b, which have structures similar to that of (-)-quinine 1.
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