Ring Distortion Diversity‐Oriented Approach to Fully Substituted Furoxans and Isoxazoles

Ring Distortion Diversity‐Oriented Approach to Fully Substituted Furoxans and Isoxazoles Full article

Journal

Asian Journal of Organic Chemistry
ISSN: 2193-5815 , E-ISSN: 2193-5807

Output data

Year: 2021, Volume: 10, Number: 10, Pages: 2644-2653 Pages count : 10 DOI: 10.1002/ajoc.202100475

Authors

Chaplygin Daniil A. ¹ , Gorbunov Yaroslav K. ^1,2 , Fershtat Leonid L. ^1,3

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 119991 Leninsky prospect, 47 Moscow Russia
2	Department of Chemistry M.V. Lomonosov Moscow State University 119991 Leninskie Gory 1-3 Moscow Russia
3	National Research University Higher School of Economics 101000 Myasnitskaya str. 20 Moscow Russia

A regioselective method for an assembly of pharmacologically relevant fully substituted furoxans and isoxazoles using the ring distortion diversity-oriented approach through the one-pot ring cleavage/nucleophilic addition/oxidation cascade of monosubstituted furoxans was developed. The described synthetic strategy is highly regioselective and provides single furoxan regioisomers upon utilization of N- or S-nucleophiles. Utilization of the cyanide-anion as a nucleophile in the same reaction cascade afforded a series of rather rare fully substituted isoxazoles incorporating vicinal nitro and amino functionalities. In addition, synthesized disubstituted furoxans revealed an ability to release NO indicating their strong potential as pharmacologically oriented drug candidates for various biomedical applications.

Chaplygin D.A. , Gorbunov Y.K. , Fershtat L.L.
Ring Distortion Diversity‐Oriented Approach to Fully Substituted Furoxans and Isoxazoles
Asian Journal of Organic Chemistry. 2021. V.10. N10. P.2644-2653. DOI: 10.1002/ajoc.202100475 WOS Scopus OpenAlex

Web of science:	WOS:000695969500001
Scopus:	2-s2.0-85114893527
OpenAlex:	W3195486333

DB	Citing
OpenAlex	7
Scopus	7
Web of science	7