One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction

Liliya Vagapova; Alexander Burilov; Almir Gazizov; Julia Voronina; Igor Litvinov; Essan Mahrous; David Virieux; Jean-Luс Pirat; Kiryll Matylitskii; Mikhail Pudovik

doi:10.1007/s10593-020-02697-2

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One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction

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One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction

Liliya Vagapova, Alexander Burilov, Almir Gazizov, Julia Voronina, Igor Litvinov, Essan Mahrous, David Virieux, Jean-Luс Pirat, Kiryll Matylitskii and Mikhail Pudovik

Chemistry of Heterocyclic Compounds, Vol.56(5), pp.542-547

05/2020

DOI: https://doi.org/10.1007/s10593-020-02697-2

Abstract

aminophosphonate

pyrrolidine

cyclization

heterocycle

The efficient approach to novel water-soluble 2-aryl-substituted N-(phosphorylmethyl)pyrrolidines via acid-catalyzed elimination/cyclization/Friedel–Crafts reaction sequence of {[(4,4-diethoxybutyl)amino]methyl}phosphonates is proposed. Zwitterionic structure of N-(phosphorylmethyl) pyrrolidines has been proved by X-ray crystallography.

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Title: One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction
Creators - without role: Liliya Vagapova - A.E. Arbuzov Institute of Organic and Physical Chemistry
Alexander Burilov - A.E. Arbuzov Institute of Organic and Physical Chemistry
Almir Gazizov - A.E. Arbuzov Institute of Organic and Physical Chemistry
Julia Voronina - Institute of General and Inorganic Chemistry
Igor Litvinov - A.E. Arbuzov Institute of Organic and Physical Chemistry
Essan Mahrous - Kazan State Technological University
David Virieux - Université de Montpellier, Institut Charles Gerhardt Montpellier - ICGM
Jean-Luс Pirat - Université de Montpellier, Institut Charles Gerhardt Montpellier - ICGM
Kiryll Matylitskii - Kazan State Technological University
Mikhail Pudovik - A.E. Arbuzov Institute of Organic and Physical Chemistry
Publication Details: Chemistry of Heterocyclic Compounds, Vol.56(5), pp.542-547
Identifiers: 9946656909311
Academic Unit: Institut Charles Gerhardt Montpellier - ICGM
Language: English
Resource Type: Journal article
Local Fields: hal-02890281