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

Liliya Vagapova (1) , Alexander Burilov (1) , Almir Gazizov (1) , Julia Voronina (2, 3) , Igor Litvinov (1) , Essan Mahrous (4) , David Virieux (5) , Jean-Luс Pirat (5) , Kiryll Matylitskii (4) , Mikhail Pudovik (1)

1 IOPC - A.E. Arbuzov Institute of Organic and Physical Chemistry
2 INEOS - A. N. Nesmeyanov Institute of Organoelement Compounds
3 IGIC - N. S. Kurnakov Institute of General and Inorganic Chemistry
4 Kazan National Research Technological University
5 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier

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.

Mots clés: aminophosphonate; pyrrolidine; cyclization; heterocycle

Domaines: Chimie organique

Liliya Vagapova, Alexander Burilov, Almir Gazizov, Julia Voronina, Igor Litvinov, et al.. One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction. Chemistry of Heterocyclic Compounds, 2020, 56 (5), pp.542-547. ⟨10.1007/s10593-020-02697-2⟩. ⟨hal-02890281⟩