Efficient assembly of mono- and bis(1,2,4-oxadiazol-3-yl)furoxan scaffolds via tandem reactions of furoxanylamidoximes

Efficient assembly of mono- and bis(1,2,4-oxadiazol-3-yl)furoxan scaffolds via tandem reactions of furoxanylamidoximes Full article

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2015, Volume: 5, Number: 58, Pages: 47248-47260 Pages count : 13 DOI: 10.1039/c5ra07295f

Authors

Fershtat Leonid L. ¹ , Ananyev Ivan V. ² , Makhova Nina N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Chemistry, Russian Academy of Sciences, 28 Vavilova str., 119991 Moscow, Russian Federation

A general, facile, highly effective one-pot protocol for the synthesis of new types of heterocyclic systems incorporating mono- and bis(1,2,4-oxadiazol-3-yl)furoxan cores based on the tandem heterocyclization of furoxanylamidoximes with various aliphatic, aromatic, and heterocyclic carboxylic acid chlorides under very mild conditions (Cs2CO3, MeCN, 20 °C) has been developed. In addition, a solvent-free approach for the (1,2,4-oxadiazol-3-yl)furoxan synthesis by the reaction of furoxanylamidoximes with trimethyl orthoformate catalyzed by Sc(OTf)3 has been achieved. The advantages of step economy and scope make these reactions a powerful tool for assembling heterocyclic scaffolds of general chemistry and biomedical interest.

Fershtat L.L. , Ananyev I.V. , Makhova N.N.
Efficient assembly of mono- and bis(1,2,4-oxadiazol-3-yl)furoxan scaffolds via tandem reactions of furoxanylamidoximes
RSC Advances. 2015. V.5. N58. P.47248-47260. DOI: 10.1039/c5ra07295f WOS Scopus OpenAlex

≡ Web of science:	WOS:000355702900097
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