The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

Erika Bálint, Ádám Tajti, Anna Ádám, István Csontos, Konstantin Karaghiosoff, Mátyás Czugler, Péter Ábrányi-Balogh, G. Keglevich

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N-H⋯O=P intermolecular hydrogen bridges pair.

Original languageEnglish
Pages (from-to)76-86
Number of pages11
JournalBeilstein Journal of Organic Chemistry
Volume13
DOIs
Publication statusPublished - Jan 12 2017

Keywords

  • Microwave
  • Pudovik reaction
  • α-aryl-α-aminophosphine oxides
  • α-aryl-α-aminophosphonates

ASJC Scopus subject areas

  • Organic Chemistry

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