Work

Direct Synthesis of Benzhydryl-Functionalized 3,4-Dihydropyridin-2-ones from 2-Pyridones and Their Use in the Formation of Bridged δ-Lactams

Year: 2024

Type: article

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.

Source: Molecules

DOI: 10.3390/molecules29225274

Authors: Zofia M Myk, Jacek G. Sośnicki, Łukasz Struk

Institutions: West Pomeranian University of Technology in Szczecin, University of Szczecin

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,069

OpenAlex ID: W4404136205

FWCI: 0.141

Cites: 39

Cited by: 1

Related to: 10