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      The Kabachnik–Fields Reaction: Mechanism and Synthetic Use

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          Abstract

          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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          Most cited references52

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

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            The Synthesis of Esters of Substituted Amino Phosphonic Acids1a

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              Aminophosphonic acids of potential medical importance.

              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.
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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                01 November 2012
                November 2012
                : 17
                : 11
                : 12821-12835
                Affiliations
                [1 ]Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
                [2 ]Research Group of the Hungarian Academy of Sciences, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
                Author notes
                [* ] Author to whom correspondence should be addressed; Email: gkeglevich@ 123456mail.bme.hu ; Tel.: +36-1-463-1111 (ext. 5883); Fax: +36-1-463-3648.
                Article
                molecules-17-12821
                10.3390/molecules171112821
                6268146
                23117425
                c32a59fe-b233-48eb-8c51-714bc89ac6c6
                © 2012 by the authors; licensee MDPI, Basel, Switzerland.

                This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                : 18 October 2012
                : 25 October 2012
                : 26 October 2012
                Categories
                Review

                kabachnik–fields reaction,α-aminophosphonates,reaction pathway,environmentally friendly,microwave,solventless

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