The kabachnik-fields reaction: Mechanism and synthetic use

G. Keglevich, Erika Bálint

Research output: Contribution to journalArticle

155 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)12821-12835
Number of pages15
JournalMolecules
Volume17
Issue number11
DOIs
Publication statusPublished - Nov 2012

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phosphine
Amines
amines
Phosphites
Imines
Microwaves
Oxides
phosphines
imines
Organophosphonates
Catalysts
microwaves
catalysts
Fourier Analysis
Bioactivity
Platinum
Ketones
oxides
Aldehydes
synthesis

Keywords

  • α-aminophosphonates
  • Environmentally friendly
  • Kabachnik-Fields reaction
  • Microwave
  • Reaction pathway
  • Solventes

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

The kabachnik-fields reaction : Mechanism and synthetic use. / Keglevich, G.; Bálint, Erika.

In: Molecules, Vol. 17, No. 11, 11.2012, p. 12821-12835.

Research output: Contribution to journalArticle

Keglevich, G. ; Bálint, Erika. / The kabachnik-fields reaction : Mechanism and synthetic use. In: Molecules. 2012 ; Vol. 17, No. 11. pp. 12821-12835.
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