Versatile approach to heteroarylfuroxan derivatives from oximinofuroxans via a one-pot, nitration/thermolysis/[3+2]-cycloaddition cascade. Issue 42 (18th October 2017)

• Record Type: Journal Article
• Authors: Larin, Alexander A.; Fershtat, Leonid L.; Ananyev, Ivan V.; Makhova, Nina N.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 42(2017)
• Page Start: 3993
• Page End: 3997
• Publication Date: 2017-10-18
• Subjects: Furoxan -- Isoxazole -- Nitrolic acids -- Thermolysis -- Nitrile oxides -- [3+2]-Cycloaddition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.09.013
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The cycloaddition reactions of furoxancarbonitrile oxides have been performed. This approach enables to obtain various N, O -heteroarylsubstituted furoxans. Target heteroarylfuroxans are formed in good yields with high regioselectivity. Abstract: 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.