The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction.
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.
MTΑ-BME Research Group for Organic Chemical Technology, 1521 Budapest, Hungary.
Erika
E
Bálint
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.
Ádám
Á
Tajti
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.
Anna
A
Ádám
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.
István
I
Csontos
Department Chemie, Ludwig-Maximilians-Universität München, 81377 München, Germany.
Konstantin
K
Karaghiosoff
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.
Mátyás
M
Czugler
Hungarian Academy of Sciences, Research Centre for Natural Sciences, Institute of Organic Chemistry, 1519 Budapest, Hungary.
Péter
P
Ábrányi-Balogh
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.
György
G
Keglevich
Pudovik reaction; microwave; α-aryl-α-aminophosphine oxides; α-aryl-α-aminophosphonates