Fluorinated 1,3,4-oxadiazoles and other azoles in cycloaddition reactions

This review covers reported cycloaddition reactions of fluorinated 1,3,4-oxadiazoles and certain other fluorinated azoles, leading to the formation of a wide range of new oxygen-containing cage structures. The considered reactions represent cascade (tandem) (2+4) cycloaddition processes leading to t...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2016-09, Vol.52 (9), p.675-686
Main Authors: Vasil’ev, Nikolai V., Kostryukova, Tatiana S., Zatonsky, Georgy V., Vatsadze, Sergey Z.
Format: Article
Language:English
Subjects:
Cascade chemical reactions
Chemistry
Chemistry and Materials Science
Cycloaddition
Fluorination
Heterocyclic compounds
Organic Chemistry
Oxadiazoles
Pharmacy
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Summary:This review covers reported cycloaddition reactions of fluorinated 1,3,4-oxadiazoles and certain other fluorinated azoles, leading to the formation of a wide range of new oxygen-containing cage structures. The considered reactions represent cascade (tandem) (2+4) cycloaddition processes leading to the formation of oxadiazabicycloheptenes, followed by retro-(2+3) cycloaddition, extrusion of nitrogen molecule, and another (2+3) cycloaddition. Preparative applications of the reactions are discussed, along with the stereochemical and orbital effects that influence their direction.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-016-1948-x