Application of Microwave Irradiation in the Synthesis of P-Heterocycles

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Abstract

This chapter summarizes the results of the Keglevich group obtained in the title subject in the last decade. In the first part, the direct esterification and other derivatizations of five- and six-ring phosphinic acids accomplished under microwave (MW) conditions are discussed. It is noteworthy that these kinds of derivatizations do not take place on conventional heating. Energetics of the above reactions evaluated by quantum chemical calculations justified the experimental results. The cyclic phosphinates were also prepared by the MW-assisted alkylating esterification of the corresponding phosphinic acids in solid-liquid phase. Applying alkyl halides of normal reactivity, the application of a phase-transfer catalyst was beneficial. Then, reactions are discussed, where the MW irradiation has a significant accelerating effect. Such reactions are the Diels-Alder reactions resulting in bridged P-heterocycles, their fragmentation-related phosphorylations and the so-called inverse Wittig-type reactions furnishing β-oxophosphoranes. The next part includes phospha-Michael additions resulting in the formation of precursors of bidentate P-ligands. Finally, the MW-assisted Kabachnik-Fields condensations affording N- and P-heterocyclic derivatives of α-aminophosphonates and α-aminophosphine oxides are summarized. It was also possible to realize bis(phospha-Mannich) reactions. A part of the bis(products) were useful in the synthesis of the corresponding ring platinum complexes. Most of the above reactions were carried out without the use of any solvent and the advantage of the MW variations was proved by comparative thermal experiments.

Original languageEnglish
Title of host publicationGreen Synthetic Approaches for Biologically Relevant Heterocycles
PublisherElsevier Inc.
Pages559-570
Number of pages12
ISBN (Electronic)9780128005903
ISBN (Print)9780128000700
DOIs
Publication statusPublished - Jan 1 2015

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Keywords

  • Derivatization
  • Diels-Alder reaction
  • Inverse Wittig reaction
  • Kabachnik-Fields reaction
  • Microwave irradiation
  • P-heterocycles
  • Phospha-Michael addition
  • Reactions
  • Synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Keglevich, G. (2015). Application of Microwave Irradiation in the Synthesis of P-Heterocycles. In Green Synthetic Approaches for Biologically Relevant Heterocycles (pp. 559-570). Elsevier Inc.. https://doi.org/10.1016/B978-0-12-800070-0.00020-7