FLUORINATED 1,3,4-OXADIAZOLES AND OTHER AZOLES IN CYCLOADDITION REACTIONS

Authors

  • Николай В. Васильев 1Moscow Region State University, 10 Radio St., Moscow 107005
  • Татьяна С. Кострюкова 2State Scientific Research Institute of Biological Engineering, 75–1 Volokolamskoe Shosse, Moscow 123424
  • Георгий В. Затонский 2State Scientific Research Institute of Biological Engineering, 75–1 Volokolamskoe Shosse, Moscow 123424
  • Сергей З. Вацадзе 3Moscow M. V. Lomonosov State University, 1 Leninskie Gory, Moscow 119991

DOI:

https://doi.org/10.1007/3343

Keywords:

fluorinated 1, 3, 4-oxadiazoles, fluorinated oxazoles, oxygen-containing cage compounds, concerted cycloaddition, (2 3) cycloaddition, (2 4) cycloaddition

Abstract

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.

Authors: Nikolai V. Vasil'ev*, Tatiana S. Kostryukova,
Georgy V. Zatonsky, Sergey Z. Vatsadze

 

Author Biographies

Николай В. Васильев, 1Moscow Region State University, 10 Radio St., Moscow 107005

Николай Валентинович Васильев

Завкафедрой теоретической и прикладной химии МГОУ

Татьяна С. Кострюкова, 2State Scientific Research Institute of Biological Engineering, 75–1 Volokolamskoe Shosse, Moscow 123424

Татьяна Сергеевна Кострюкова

Георгий В. Затонский, 2State Scientific Research Institute of Biological Engineering, 75–1 Volokolamskoe Shosse, Moscow 123424

Георгий Валерьевич Затонский

Сергей З. Вацадзе, 3Moscow M. V. Lomonosov State University, 1 Leninskie Gory, Moscow 119991

Московский государственный университет им. М. В. Ломоносова,
Ленинские горы, 1, Москва 119991, Россия

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Published

2016-10-25

Issue

Vol. 52 No. 9 (2016): Pericyclic reactions in heterocyclic chemistry

Section

Review Articles