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

Bálint, Erika; Tajti, Ádám; Ádám, Anna; Csontos, István; Karaghiosoff, Konstantin; Czugler, Mátyás; Ábrányi-Balogh, Péter und Keglevich, György (2017): The synthesis of alpha-aryl-alpha-aminophosphonates and alpha-aryl-alpha-aminophosphine oxides by the microwave-assisted Pudovik reaction. In: Beilstein Journal of Organic Chemistry, Bd. 13: S. 76-86

Abstract

A family of alpha-aryl-alpha-aminophosphonates and alpha-aryl-alpha-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 alpha-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N-H center dot center dot center dot O=P intermolecular hydrogen bridges pair.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1860-5397
• Sprache: Englisch