Direct Synthesis of Benzhydryl-Functionalized 3,4-Dihydropyridin-2-ones from 2-Pyridones and Their Use in the
Zofia M Myk1, Jacek G Sośnicki1, Łukasz Struk1,2
1Department of Organic and Physical Chemistry, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technologyin Szczecin, Al. Piastów 42, 71-065 Szczecin, Poland.
Abstract:
A method for the synthesis of C4-benzhydryl-functionalized 3,4-dihydropyridin-2-ones using complementary addition of benzhydryllithium and/or benzhydrylmagnesiate reagents to 2-pyridones, with high regioselectivity triggered by substituents, is described. A partially stereoselective cyclization was successfully demonstrated using TfOH and/or TIPSOTf as Brønsted and Lewis acids, respectively, leading to C6-phenyl-functionalized 7,8-benzomorphanones. It is also shown that the use of functionalized δ-enelactams obtained with an active methoxy-substituted benzyl group at C3 enabled the preparation of a new C3-C6 bridged system within the δ-lactam framework.
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