Version 1
: Received: 7 October 2024 / Approved: 8 October 2024 / Online: 8 October 2024 (10:20:32 CEST)
How to cite:
Myk, Z. M.; Sośnicki, J. G.; Struk, Ł. Direct Synthesis of Benzhydryl-Functionalized 3,4-Dihydropyridin-2-Ones from 2-Pyridones and Their Use in the Formation of Bridged -Lactams. Preprints2024, 2024100534. https://doi.org/10.20944/preprints202410.0534.v1
Myk, Z. M.; Sośnicki, J. G.; Struk, Ł. Direct Synthesis of Benzhydryl-Functionalized 3,4-Dihydropyridin-2-Ones from 2-Pyridones and Their Use in the Formation of Bridged -Lactams. Preprints 2024, 2024100534. https://doi.org/10.20944/preprints202410.0534.v1
Myk, Z. M.; Sośnicki, J. G.; Struk, Ł. Direct Synthesis of Benzhydryl-Functionalized 3,4-Dihydropyridin-2-Ones from 2-Pyridones and Their Use in the Formation of Bridged -Lactams. Preprints2024, 2024100534. https://doi.org/10.20944/preprints202410.0534.v1
APA Style
Myk, Z. M., Sośnicki, J. G., & Struk, Ł. (2024). Direct Synthesis of Benzhydryl-Functionalized 3,4-Dihydropyridin-2-Ones from 2-Pyridones and Their Use in the Formation of Bridged -Lactams. Preprints. https://doi.org/10.20944/preprints202410.0534.v1
Chicago/Turabian Style
Myk, Z. M., Jacek G. Sośnicki and Łukasz Struk. 2024 "Direct Synthesis of Benzhydryl-Functionalized 3,4-Dihydropyridin-2-Ones from 2-Pyridones and Their Use in the Formation of Bridged -Lactams" Preprints. https://doi.org/10.20944/preprints202410.0534.v1
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 -enelactams obtained with an active methoxy-substituted benzyl group at C3, enabled the preparation of a new C3-C6 bridged system within -lactam framework.
Chemistry and Materials Science, Organic Chemistry
Copyright:
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