Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions

Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2022, Volume: 364, Number: 15, Pages: 2606-2612 Pages count : 7 DOI: 10.1002/adsc.202200420

Authors

Antonova Yulia A. ^1,2 , Nelyubina Yulia V. ³ , Ioffe Sema L. ¹ , Sukhorukov Alexey Yu. ¹ , Tabolin Andrey A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991 Russian Federation
2	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1, Moscow, 119991 Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow, 119991, Russian Federation

Acylation of nitroalkylmalonates was found to yield substituted isoxazoline derivatives. This redox-neutral transformation has a wide substrate scope and produces target products with yields up to 92%. Various substituents (aryl, alkyl, and ester) at the C3 and C4 positions of the resulting isoxazolines were also tolerated. A quick assembly of the isoxazoline ring starting from nitroalkenes and malonates was successfully developed. Control experiments showed that the intramolecular ring closure is the most likely key mechanistic step. Subsequent transformations into pyrrolidine and furane derivatives demonstrated the synthetic utility of the obtained products.

Antonova Y.A. , Nelyubina Y.V. , Ioffe S.L. , Sukhorukov A.Y. , Tabolin A.A.
Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions
Advanced Synthesis & Catalysis. 2022. V.364. N15. P.2606-2612. DOI: 10.1002/adsc.202200420 WOS Scopus OpenAlex

Web of science:	WOS:000821073700001
Scopus:	2-s2.0-85133417211
OpenAlex:	W4283455261

DB	Citing
OpenAlex	9
Scopus	10
Web of science	8