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      Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles

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          Abstract

          In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and N-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided.

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          Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.

          Artur Mucha, Paweł Kafarski, Łukasz Berlicki (2011)
          Article 0 comments Cited 74 times – based on 0 reviews     Review now
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            Aminophosphonic acids of potential medical importance.

            B Lejczak, P Kafarski (2001)
            Aminophosphonic acids were almost unknown in 1959 but today they are the subject of more than 6000 papers. Their negligible mammalian toxicity, and the fact that they very efficiently mimic aminocarboxylic acids makes them extremely important antimetabolites, which compete with their carboxylic counterparts for the active sites of enzymes and other cell receptors. Although biological importance of these compounds was recognized over 50 years ago they still represent promising and somewhat undiscovered class of potential drugs.
            Article 0 comments Cited 38 times – based on 0 reviews     Review now
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              The Kabachnik–Fields Reaction: Mechanism and Synthetic Use

              György Keglevich, Erika Bálint (2012)
              The Kabachnik–Fields (phospha-Mannich) reaction involving the condensation of primary or secondary amines, oxo compounds (aldehydes and ketones) and >P(O)H species, especially dialkyl phosphites, represents a good choice for the synthesis of α-aminophosphonates that are of significant importance due to their biological activity. In general, these three-component reactions may take place via an imine or an α-hydroxy-phosphonate intermediate. The monitoring of a few Kabachnik–Fields reactions by in situ Fourier transform IR spectroscopy has indicated the involvement of the imine intermediate that was also justified by theoretical calculations. The Kabachnik–Fields reaction was extended to >P(O)H species, comprising cyclic phosphites, acyclic and cyclic H-phosphinates, as well as secondary phosphine oxides. On the other hand, heterocyclic amines were also used to prepare new α-amino phosphonic, phosphinic and phosphine oxide derivatives. In most cases, the synthesis under solvent-free microwave (MW) conditions is the method of choice. It was proved that, in the cases studied by us, there was no need for the use of any catalyst. Moreover, it can be said that sophisticated and environmentally unfriendly catalysts suggested are completely unnecessary under MW conditions. Finally, the double Kabachnik–Fields reaction has made available bis(phosphonomethyl)amines, bis(phosphinoxidomethyl)amines and related species. The bis(phosphinoxidomethyl)amines serve as precursors for bisphosphines that furnish ring platinum complexes on reaction with dichlorodibenzonitriloplatinum.
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                Author and article information

                Contributors
                Erika Bálint: Role: Academic Editor
                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 19 September 2019
                Publication date Collection: September 2019
                Volume: 24
                Issue: 18
                Electronic Location Identifier: 3405
                Affiliations
                [1 ]Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland stec-k@ 123456o2.pl (K.S.); krzysztof.walczak@ 123456polsl.pl (K.W.)
                [2 ]Biotechnology Center of Silesian University of Technology, B. Krzywoustego 8, 44-100 Gliwice, Poland
                [3 ]Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland; karol.erfurt@ 123456polsl.pl
                Author notes
                [* ]Correspondence: jakub.adamek@ 123456polsl.pl ; Tel.: +48-032-237-1080; Fax: +48-032-237-2094
                Author information
                https://orcid.org/0000-0002-2960-6247
                https://orcid.org/0000-0001-8511-2009
                Article
                Publisher ID: molecules-24-03405
                DOI: 10.3390/molecules24183405
                PMC ID: 6767244
                PubMed ID: 31546826
                SO-VID: 69f75cc3-aae2-4579-beb6-b8a47019de01
                Copyright © © 2019 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 09 September 2019
                Date accepted : 16 September 2019
                Categories
                Subject: Article

                Keywords: organophosphorus chemistry,phosphonium salts,phosphonates,phosphinates,phosphine oxides
                Data availability:
                Keywords: organophosphorus chemistry, phosphonium salts, phosphonates, phosphinates, phosphine oxides

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