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3,3-Diazidoenones – new types of highly reactive bis-azides. Preparation and synthetic transformations

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Abstract

The interaction of geminal dichlorovinylketones with sodium azide was investigated by NMR and DFT calculations. It was found that the corresponding geminal 3,3-diazidoenones are the resultant species. These highly reactive compounds can be trapped with cyclooctyne to form bis-triazolyl substituted enones. In the absence of a trapping agent, 3,3-diazidoenones do cyclize into 3-azidoisoxazoles with the elimination of molecular nitrogen. The versatile reactivity of the resultant azidoisoxazoles was demonstrated in reactions with phosphorus(III) derivatives, Huisgen 1,3-dipolar cycloaddition and Dimroth cyclization to provide efficient access to a variety of valuable compounds.

Graphical abstract: 3,3-Diazidoenones – new types of highly reactive bis-azides. Preparation and synthetic transformations

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The article was received on 09 Nov 2018, accepted on 08 Dec 2018 and first published on 10 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01214H
Citation: Org. Chem. Front., 2019, Advance Article
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    3,3-Diazidoenones – new types of highly reactive bis-azides. Preparation and synthetic transformations

    P. S. Lemport, I. V. Smolyar, V. N. Khrustalev, V. A. Roznyatovsky, A. V. Popov, V. A. Kobelevskaya, I. B. Rozentsveig and V. G. Nenajdenko, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01214H

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