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Updated: Jul 11, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Quinine synthesis studies: a radical-ionic annulation via Mn-mediated addition to chiral N-acylhydrazones
Chandra Sekhar Korapala1, Jun Qin, Gregory K Friestad
1Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA.
Abstract:
A radical-ionic annulation approach to functionalized perhydroisoquinolines involving Mn-mediated coupling of alkyl iodides and chiral N-acylhydrazones was achieved using only 1.25 equiv of the alkyl iodide. Application of this reaction to alkene-containing substrates en route to quinine offered modest yields, decreasing on scaleup. Control experiments revealed that the alkene interfered with the coupling reaction. A revised approach involving prior oxidation of the alkene offered 93% yield in the Mn-mediated coupling, with the adduct obtained as a single diastereomer.
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