Versatile approach to heteroarylfuroxan derivatives from oximinofuroxans via a one-pot, nitration/thermolysis/[3+2]-cycloaddition cascade

Versatile approach to heteroarylfuroxan derivatives from oximinofuroxans via a one-pot, nitration/thermolysis/[3+2]-cycloaddition cascade Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2017, Volume: 58, Number: 42, Pages: 3993-3997 Pages count : 5 DOI: 10.1016/j.tetlet.2017.09.013

Authors

Larin Alexander A. ¹ , 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 Compounds, Russian Academy of Sciences, 28, Vavilova Str., 119991 Moscow, Russian Federation

A simple, general, and regioselective method has been developed for the synthesis of a series of heteroarylfuroxans, including isoxazolyl-, isoxazolinyl- and (1,2,4-oxadiazolyl)furoxans. The described method is based on a cascade of one-pot processes, including the nitration of furoxancarbaldehyde oximes, thermolysis of the formed nitrolic acids to generate furoxancarbonitrile oxides, and [3+2]-cycloaddition with an appropriate dipolarophile – alkynes, olefins, or activated nitriles.

Larin A.A. , Fershtat L.L. , Ananyev I.V. , Makhova N.N.
Versatile approach to heteroarylfuroxan derivatives from oximinofuroxans via a one-pot, nitration/thermolysis/[3+2]-cycloaddition cascade
Tetrahedron Letters. 2017. V.58. N42. P.3993-3997. DOI: 10.1016/j.tetlet.2017.09.013 WOS Scopus OpenAlex

Web of science:	WOS:000413283800011
Scopus:	2-s2.0-85029479580
OpenAlex:	W2752200020

DB	Citing
OpenAlex	17
Scopus	17
Web of science	15