Synthesis of Novel 2-Hetarylpyrrolidines via the Reaction of N-(4,4-diethoxybutyl)amidophosphates with C-nucleophiles

© 2020, Springer Science+Business Media, LLC, part of Springer Nature. [Figure not available: see fulltext.] The reactions of N-(4,4-diethoxybutyl)amidophosphates with С-nucleophiles in chloroform in the presence of trifluoroacetic acid provided new 2-hetarylpyrrolidines. The reaction proceeded under mild conditions and gave good yields in the absence of metal-based catalysts

Reaction of N-(4,4-Diethoxybutyl)phosphamides with Chloro(diphenyl)phosphine. Synthesis of 2-(Diphenylphosphoryl)pyrrolidines

© 2020, Pleiades Publishing, Ltd. Abstract: The reaction of N-(4,4-diethoxybutyl)phosphamides with chloro(diphenyl)phosphine in chloroform in the presence of acetic acid gave previously unknown 2-(diphenylphosphoryl)pyrrolidines, and hydrolysis of the latter afforded 2-(diphenylphosphoryl)pyrrolidine

N-Phosphorylated Pyrrolidines: An Overview of Synthetic Approaches

© 2020 Georg Thieme Verlag. All rights reserved. Organophosphorus pyrrolidine derivatives possessing P-N bonds are a promising yet underexplored class of compounds. In this short review we overview the general approaches to these compounds described so far, with a special emphasis on their asymmetric synthesis. 1 Introduction 2 Synthesis of Pyrrolidine-Based P(III) Derivatives 3 Synthesis of Pyrrolidine-Based P(V) Derivatives 3.1 Phosphorylation of Pyrrolidines with P(V) Acid Chlorides 3.2 Phosphorylation of Pyrrolidines with P(V) Acid Esters 3.3 Syntheses via the Atherton-Todd Reaction 3.4 Oxidation of Pyrrolidine-Based P(III) Derivatives 4 Syntheses of N-Phosphorylpyrrolidines from Acyclic Precursors 5 Conclusions

Reaction of 3-(Arylmethylidene)-1-pyrrolines with Acetone. Synthesis of Norhygrine Derivatives

© 2020, Pleiades Publishing, Ltd. Abstract: An efficient procedure has been developed for the synthesis of analogs of the alkaloid norhygrine by reaction of 3-(arylmethylidene)-1-pyrrolines with acetone. The synthesized compounds have been converted to hydrazones by treatment with the corresponding substituted arylhydrazines

Synthesis of New α-Aminophosphonates Based on Cyclohexylamine

© 2020, Pleiades Publishing, Ltd. Abstract: A series of new α-aminophosphonates was synthesized based on the acid-catalyzed Kabachnik–Fields reaction involving diethyl phosphite, cyclohexylamine and substituted benzaldehyde. Structure of the reaction products was established by IR, NMR spectroscopy, and mass spectrometry methods

2-(Het)aryl-N-phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach

© 2020 Wiley-VCH GmbH A first successful synthesis of 2-(het)aryl-N-phosphorylpyrrolidines is reported starting from readily available N-(4,4-diethoxybutyl)amides of P(V) acids. A range of phenols and hydroxyl-substituted O-heterocycles may be employed into the reaction furnishing N-phosphorylated 2-(het)arylpyrrolidines with up to 90 % yield. The developed method permits a presence of sensitive to phosphorylation hydroxy groups and provides the easy and regioselective entry to target compounds

The highly regioselective synthesis of novel imidazolidin-2-ones via the intramolecular cyclization/electrophilic substitution of urea derivatives and the evaluation of their anticancer activity

A series of novel 4-(het)arylimidazoldin-2-ones were obtained by the acid-catalyzed reaction of (2,2-diethoxyethyl)ureas with aromatic and heterocyclic C-nucleophiles. The proposed approach to substituted imidazolidinones benefits from excellent regioselectivity, readily available starting materials and a simple procedure. The regioselectivity of the reaction was rationalized by quantum chemistry calculations and control experiments. The anti-cancer activity of the obtained compounds was tested in vitro