Concise approach to γ-(het)aryl- and γ-alkenyl-γ-aminobutyric acids. Synthesis of vigabatrin

Concise approach to γ-(het)aryl- and γ-alkenyl-γ-aminobutyric acids. Synthesis of vigabatrin Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2024, Volume: 22, Number: 5, Pages: 1027-1033 Pages count : 7 DOI: 10.1039/d3ob01769a

Authors

Plodukhin Andrey Yu. ¹ , Boichenko Maksim A. ¹ , Andreev Ivan A. ^2,3 , Tarasenko Elena A. ¹ , Anisovich Kanstantsin V. ¹ , Ratmanova Nina K. ^2,3 , Zhokhov Sergey S. ¹ , Trushkov Igor V. ³ , Ivanova Olga Alexandrovna ¹

Affiliations

1	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russia
2	Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow 117997, Russia
3	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia

γ-Aminobutyric acid (GABA) and GABA derivatives have attracted increased attention over the years in the fields of medicinal chemistry and chemical biology due to their interesting biological properties and synthetic relevance. Here, we report a short synthetic route to γ-(het)aryl- and γ-alkenyl-γ-aminobutyric acids, including the antiepileptic drug vigabatrin, from readily available donor–acceptor cyclopropanes and ammonia or methylamine. This protocol includes a facile synthesis of 2-oxopyrrolidine-3-carboxamides and their acid hydrolysis to γ-aryl- or γ-alkenyl-substituted GABAs, which can serve as perspective building blocks for the synthesis of various GABA-based N-heterocycles and bioactive compounds.

Plodukhin A.Y. , Boichenko M.A. , Andreev I.A. , Tarasenko E.A. , Anisovich K.V. , Ratmanova N.K. , Zhokhov S.S. , Trushkov I.V. , Ivanova O.A.
Concise approach to γ-(het)aryl- and γ-alkenyl-γ-aminobutyric acids. Synthesis of vigabatrin
Organic & Biomolecular Chemistry. 2024. V.22. N5. P.1027-1033. DOI: 10.1039/d3ob01769a WOS Scopus OpenAlex

Web of science:	WOS:001138229600001
Scopus:	2-s2.0-85182361035
OpenAlex:	W4390363288

DB	Citing
OpenAlex	5
Scopus	5
Web of science	4