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

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. © 2019 the Partner Organisations.

Авторы
Lemport P.S.1 , Smolyar I.V.1 , Khrustalev V.N. 2 , Roznyatovsky V.A.1 , Popov A.V.3 , Kobelevskaya V.A.3 , Rozentsveig I.B.3 , Nenajdenko V.G. 1
Издательство
Royal Society of Chemistry
Номер выпуска
3
Язык
Английский
Страницы
335-341
Статус
Опубликовано
Том
6
Год
2019
Организации
  • 1 Department of Chemistry, Lomonosov Moscow State University, Moscow, 119991, Russian Federation
  • 2 Department of Inorganic Chemistry, Peoples' Friendship University of Russia, Russian Federation
  • 3 A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Russian Federation
Ключевые слова
1 ,3-Dipolarcycloaddition; DFT calculation; Molecular nitrogen; Synthetic transformations; Trapping agent; Sodium Azide
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