Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans

Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans Full article

Journal

Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881

Output data

Year: 2020, Volume: 52, Number: 18, Pages: 2667-2678 Pages count : 12 DOI: 10.1055/s-0040-1707393

Authors

Chaplygin Daniil A. ¹ , Ananyev Ivan V. ^2,3 , Fershtat Leonid L. ¹ , Makhova Nina N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
3	National Research University Higher School of Economics

A novel method for the synthesis of a diverse series of functionally substituted five-membered heterocyclic compounds via atom-economic, regio-, and diastereoselective one-pot reaction cascade was developed. This approach involves a ring opening in 4-arylfuroxans to α-oximinoarylacetonitrile oxides followed by [3+2] cycloaddition to various dipolarophiles to afford multisubstituted isoxazoles and isoxazolines. Subsequent azole–azole rearrangement of (oximino)isoxazolines/-isoxazoles, which can be conducted in a one-pot manner, results into functionally substituted furazans formation. The developed protocol is operationally simple, proceeds in mild conditions and with high yields of target heterocyclic systems. Overall, this study represents a new mode of isoxazole and 1,2,5-oxadiazole functionalization strategy, which is useful in medicinal and materials chemistry.

Chaplygin D.A. , Ananyev I.V. , Fershtat L.L. , Makhova N.N.
Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans
Synthesis-Stuttgart. 2020. V.52. N18. P.2667-2678. DOI: 10.1055/s-0040-1707393 WOS Scopus OpenAlex

Web of science:	WOS:000563008300008
Scopus:	2-s2.0-85094612730
OpenAlex:	W3022246437

DB	Citing
OpenAlex	13
Scopus	11
Web of science	10