One-pot synthesis of N-phosphorylmethyl pyrrolidines via an acid-catalyzed cascade elimination / cyclization / Friedel-Crafts reaction

Authors

  • Liliya I. Vagapova Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center ''Kazan Scientific Center of the Russian Academy of Sciences'', 8 Akademika Arbuzova St., 8, Kazan 420088, Russia
  • Alexander R. Burilov Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center ''Kazan Scientific Center of the Russian Academy of Sciences'', 8 Akademika Arbuzova St., 8, Kazan 420088, Russia
  • Almir S. Gazizov Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center ''Kazan Scientific Center of the Russian Academy of Sciences'', 8 Akademika Arbuzova St., 8, Kazan 420088, Russia
  • Julia K. Voronina N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences 31 Leninsky Ave., Moscow 119991, Russia A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991, Russia
  • Igor A. Litvinov Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center ''Kazan Scientific Center of the Russian Academy of Sciences'', 8 Akademika Arbuzova St., 8, Kazan 420088, Russia
  • Essan M. Mahrous Kazan National Research Technological University, 68 Karl Marks St., Kazan 420015, Russia
  • David Virieux ICGM, Univ Montpellier, ENSCM, CNRS, Montpellier Institut Charles Gerhardt, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France
  • Jean-Luс Pirat ICGM, Univ Montpellier, ENSCM, CNRS, Montpellier Institut Charles Gerhardt, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France
  • Kiryll Matylitskii
  • Mikhail Pudovik

DOI:

https://doi.org/10.1007/5523

Keywords:

cyclization, pyrrolidine, heterocycle, aminophosphonate

Abstract

Был разработан эффективный подход к синтезу новых водорастворимых N-метилфосфорилпирролидинов на основе кислотно-катализируемой внутримолекулярной циклизации/реакции Фриделя-Крафтса (4,4-диэтоксибутиламинометил)фосфонатов. Цвиттер-ионная природа пирролдидинилметилфосфонатов была подтверждена данными рентгеноструктурного анализа.

The efficient approach to novel water-soluble N-methylphosphoryl-pyrrolidines via acid-catalyzed elimination/cyclization/Friedel-Crafts reaction sequence of (4,4-diethoxybutylaminomethyl)-phosphonates is proposed. Zwitterionic structure of pyrrolidinylmethyl phosphonates has been proved by X-Ray crystallography.

Author Biography

Liliya I. Vagapova, Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center ''Kazan Scientific Center of the Russian Academy of Sciences'', 8 Akademika Arbuzova St., 8, Kazan 420088, Russia

Научный сотрудник, к.х.н. ,  лаборатоии элементоорганического синтеза им. А.Н. Пудовика (Институт органической и физической химии им. А.Е. Арбузова ФИЦ Казанский научный центр РАН)

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Published

2020-05-28

Issue

Vol. 56 No. 5 (2020)

Section

Original Papers