1. Synthesis of 1,5-Substituted Pyrrolidin-2-ones from Donor-Acceptor Cyclopropanes and Anilines/Benzylamines.
- Author
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Boichenko MA, Plodukhin AY, Shorokhov VV, Lebedev DS, Filippova AV, Zhokhov SS, Tarasenko EA, Rybakov VB, Trushkov IV, and Ivanova OA
- Subjects
- Molecular Structure, Cyclopropanes chemistry, Lewis Acids chemistry, Amines chemistry, Aniline Compounds, Benzylamines
- Abstract
We developed a straightforward synthetic route to pharmacologically important 1,5-substituted pyrrolidin-2-ones from donor-acceptor cyclopropanes bearing an ester group as one of the acceptor substituents. This method includes a Lewis acid-catalyzed opening of the donor-acceptor cyclopropane with primary amines (anilines, benzylamines, etc.) to γ-amino esters, followed by in situ lactamization and dealkoxycarbonylation. The reaction has a broad scope of applicability; a variety of substituted anilines, benzylamines, and other primary amines as well as a wide range of donor-acceptor cyclopropanes bearing (hetero)aromatic or alkenyl donor groups and various acceptor substituents can be involved in this transformation. In this process, donor-acceptor cyclopropanes react as 1,4- C , C -dielectrophiles, and amines react as 1,1-dinucleophiles. The resulting di- and trisubstituted pyrrolidin-2-ones can be also used in subsequent chemistry to obtain various nitrogen-containing polycyclic compounds of interest to medicinal chemistry and pharmacology, such as benz[ g ]indolizidine derivatives., Competing Interests: The authors declare no conflict of interest.
- Published
- 2022
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