Synthesis of 1,5-Substituted Pyrrolidin-2-ones from Donor–Acceptor Cyclopropanes and Anilines/Benzylamines

Synthesis of 1,5-Substituted Pyrrolidin-2-ones from Donor–Acceptor Cyclopropanes and Anilines/Benzylamines Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2022, Volume: 27, Number: 23, Article number : 8468, Pages count : DOI: 10.3390/molecules27238468

Authors

Boichenko Maksim A. ¹ , Plodukhin Andrey Yu. ¹ , Shorokhov Vitaly V. ¹ , Lebedev Danyla S. ¹ , Filippova Anastasya V. ¹ , Zhokhov Sergey S. ¹ , Tarasenko Elena A. ¹ , Rybakov Victor B. ¹ , Trushkov Igor V. ² , Ivanova Olga A. ¹

Affiliations

1	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Leninsky Pr. 47, 119334 Moscow, Russia

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.

Boichenko M.A. , Plodukhin A.Y. , Shorokhov V.V. , Lebedev D.S. , Filippova A.V. , Zhokhov S.S. , Tarasenko E.A. , Rybakov V.B. , Trushkov I.V. , Ivanova O.A.
Synthesis of 1,5-Substituted Pyrrolidin-2-ones from Donor–Acceptor Cyclopropanes and Anilines/Benzylamines
Molecules. 2022. V.27. N23. 8468 . DOI: 10.3390/molecules27238468 WOS Scopus OpenAlex

Web of science:	WOS:000897495900001
Scopus:	2-s2.0-85143643878
OpenAlex:	W4311533622

DB	Citing
OpenAlex	11
Scopus	9
Web of science	9